154 HB Nuclear Magnetic Resonance Spectroscopy of Boron-Nitrogen Compounds

Appendix

11 B Nuclear Magnetic Resonance Spectroscopy of Boron-Nitrogen Compounds

A. General Remarks

The element boron has two naturally occurring isotopes; the natural abundance of lOB is 18.3%, that of HB is 81.7%. Both nuclei have magnetic moments, but normally only the effects of the boron isotope lIB are considered in boron nuclear magnetic resonance studies. The HB atom has a spin of I = 3/2. The first lIB resonance studies were reported by OGG1 and SHOOLERy2, 3; HB nuclear magnetic resonance spectro• scopy has played an important part in the structural determination of boron hydrides4 • In a qualitative and somewhat simplified approach, the major features of the lIB chemical shifts can be accounted for on the basis of a paramagnetic shift. This shift arises from the difference in electron occupancy of the bonding Px and Py orbitals and the partially filled pz orbital. Neglecting hyperconjugation, the bonding hybrid of boron in trimethylborane, B(CH3la, should be Sp2 with a vacant pz orbital. This characteristic accounts for low field resonance in the lIB nuclear magnetic resonance spectrum. In other molecules of the type BR3, contributions from electrons of atoms bonded to boron provide partial double bond character between the boron and its substituent. Thus the valence shell of boron approaches an electron octet and the lIB chemical shift moves toward a higher field. At the other end of the spectrum, opposed to trimethylborane, the lIB resonance of the hydro• borate anion, BH'r, should be at its highest field. The hydroborate ion presumably exists as a Sp3 bonding hybrid of boron with full tetra• hedral symmetry about that atom. This situation is evidenced by high field HB nuclear magnetic resonance. If the effect of the paramagnetic shift governs shielding of boron, the lIB chemical shifts of all boron compounds should be expected to fall between the values of trimethylborane at low field and the hydro• borate ion at high field, an area which stretches over about 130 X 10-6• Indeed, all boron compounds which have been studied thus far with HB nuclear magnetic resonance spectroscopy have their HB chemical shift values between these two. The only exceptions known are the

1 OGG, R. A.: J. chern. Physics 22, 1933 (1954). 2 SnOOLERY, J. N.: Disc. Faraday Soc. 19, 215 (1955). 3 SCHAEFFER, R., J. N. SnOOLERY and R. JONES: J. Amer. chern. Soc. 79, 4606 (1957). 4 LIPSCOMB, W. N.: "Boron Hydrides", W. A. Benjamin, Inc., New York• Amsterdam, 1963. A. General Remarks 155 apex atom in BsH9 and some triiodoborane complexes!, which exhibit their llB resonance at even higher field than the hydroborate ion. Solvent effects upon the chemical shifts of llB resonance spectra appear to be negligible, except, of course, when chemical reaction occurs between the boron compound and the solvent. Therefore, the llB chemical shift of a boron compound can be regarded as a characteristic constant for identification purposes. The diethyletherate of trifluoroborane, (C2Hs)20 . BF3, is normally used as the zero reference for llB chemical shift data, because of the sharp resonance line and the ready availability of the compound. However, in many instances, trimethoxyborane, B(OCH3h, has been used. The chemical shifts of these two major zero references for llB resonance spectroscopy differ by a value of + 18.1 X 10-6 for the etherate of trifluoroborane relative to that of trimethoxyborane. The two major groups of llB chemical shifts as described above (i.e. Sp2 or Sp3 hybridization) can be characterized further on the basis of inductive effects of the atoms bonded directly to boron, since non• adjacent atoms have little effect on the shielding. On this basis, certain series of llB chemical shifts can be observed. They are essentially in agreement with the polar bond theory which requires that shifts become more negative as the electronegativity of the substituents increases. This situation is illustrated by the fact that the shielding of a boron nucleus in the trihalogenoborane series decreases in the order BI3 > BBr3 > BCl3. Only trifluoroborane exists as a exception. The high shielding of boron in trifluoroborane can readily be explained in terms of the increased ionic character of this compound through partial formation of a B-F double bond, i.e. occupation of pz orbitals of boron by non• bonding electrons of the fluorine atoms. Summarizing, there are two main factors which contribute to the shielding of boron nuclei and thus to the actual values of HB chemical shift data. Of major importance is hybridization of the boron in the direction Sp2 -7 Sp3 in conformance with a chemical shift to higher field. However, the electronegativity of ligands plays a distinct. role in the nuclear shielding of boron atoms. - There are no references available on nitrogen resonance studies of boron-nitrogen compounds. A comparison of spin-spin coupling constants between boron and hydrogen in a variety of boron compounds illustrates that the coupling constants are smaller if hybridized Sp3 orbitals are used for bonding instead of Sp2 orbitals. Thus a constant J BH = 81 cps. is found for the hydroborate anion, whereas in borazine, (-BH-NH-)3' it is 136 cps. Coupling constants between these two values have been measured for those derivatives of the hypothetical BH3 where one assumes a boron hybridization between Sp2 and Sp3. In general, the widths of llB reso• nance lines are considerable due to quadrupole relaxation effects. Con• sequently, spin-spin coupling between boron and hydrogen beyond atoms

1 LANDESMAN, H., and R. E. WILLIAMS: J. Amer. chern. Soc. 83, 2663 (1961). 156 HB Nuclear Magnetic Resonance Spectroscopy of Boron-Nitrogen Compounds bonded directly to each other has not been observed. In view of the wide lines, the half-band widths of llB resonances are often cited in conjunction with chemical shift data.

B.llB Nuclear Magnetic Resonance of Boron-Nitrogen Compounds

When closely related compounds are involved, the value of the llB chemical shift may be considered roughly proportional to the electron shielding around a boron nucleus. Higher chemical shift values thus inrucate greater electronic shielrung around the boron. In the case of boron-nitrogen compounds, this condition appears to correspond to in• creased boron-nitrogen bonding. Some specific applications of llB nuclear magnetic resonance spectroscopy have been discussed in previous chapters. Hence the following description is limited to some general considerations. Borazines. As is evident from the chemical shift values of the HB resonance of borazines, the shielding of a boron nucleus in such molecules is somewhat greater than that in trialkylboranes. This increased shield• ing can be related to an electron delocalisation: Lone-pair electrons of the nitrogen atoms participate in the bonding between boron and nitrogen, thus providing for resonance structures as discussed previously (Chapter III). Chemical shift values for borazines have been reported in the range from about - 32 to - 22 X 10-6• Aminoboranes. Physical and chemical evidence suggests the ex• istence of double bond character for the boron-nitrogen bond in mono• meric aminoboranes. This is evidenced in their llB resonance spectra through observation of a llB chemical shift to higher field than one finds with trisubstituted boranes such as trialkylboranes. The llB chemical shift of organic substituted aminoboranes is found in the - 45 to - 35 X 10-6 region. Dimerization changes the enviromnent of the boron atom (see Chapter II) and the chemical shift of a dimeric aminoborane is normally found near -10 X 10-6 to o. Hence llB chemical shift data can be used for analytical purposes in those cases where partial dimerization takes place: Relative intensities of high and low field HB resonances permit elaboration of the monomer-dimer ratio. The llB chemical shift values of trimeric aminoboranes are centered around 0 to + 10 X 10-6. Amine-Boranes. Formation of an amine adduct with a BR3 entity is accompanied by a change of boron hybriruzation presumably from Sp2 to Sp3. This denotes partial electron occupation of the boron P2 orbital through donation of the lone-pair electrons from nitrogen. This event is confirmed by the observation of a reduced paramagnetic shift of B. HB Nuclear Magnetic Resonance of Boron-Nitrogen Compounds 157

Table 1. HE Ohemical Shift Data

Compound Solvent X 10-" IReferences B(CHa)a neat -S6.3 6,7 B(C2H s)a neat -S4.7 (-BH-NCHa-la neat -32.4 (-BH-NH-la neat -30.4 (-BCHCH2-NH-)a neat -31.S {-BF-NH-la benzene -25.1 (-BF-NCHa-)a benzene -24.3 {-BF-NCaH7-)a benzene -23.1 neat {-47.5} {C2Hs)2N-BHC4Hs (i) -38.1 neat { -48.5} (CHa)2N-BHC4Hs (t) -38.7 (CHa)2N-B(C4Hs)2 neat -45.3 (CHa) (C6HS)N-B(CHa) (C6H 5) neat -44.3 n-C4HSB[N(CHa)2Jz neat -34.2 n-C4HsB[N(C2H 5)2Jz neat -39.3 CsHsB[N (CHa)2Jz neat -32.4 B[N(CHa)2J3 neat -27.1 B[N(C 2Hs)2J3 neat· -31.0 {-S.4} [HaCHN-BHC4Hs(t)J2 neat -0.1 {-BH2-NHz-)a ammonia +11.3 (-BHz-NHCHa-la methanol +5.8 (-BCI2-NH2-)a diglyme -6.9 (-BHCI-NHCHa-)3 chloroform -1.1

B2H 4[N(CHa)2J2 neat +18.6 BZH 5N(CH3Jz neat -3.6 (CHa)aN. BF3 benzene/methanol +0.5 HaN. BF3 water +2.1 piperidine. BFa carbon disulfide +2.3 NH4BF4 water +1.8 (CH3)3N . BH3 benzene +9.1 (CRa)2HN. BRa benzene +15.1 pyridine. BHa neat {+13.3} +11.5 NaBH4 0.1 nNaOH +42.9 water +38.7

1 BAECHLE, H., H. J. BECHER, H. BEYER, W. S. BREY, J. W. DAWSON, M. E. FULLER II and K. NIEDENZU, Inorg. Chern. 2, 1065 (1963). 2 FRITZ, P., K. NIEDENZU and J. W. DAWSON: ibid. 3, 626 (1964). 3 GAINES, D. F., and R. SCHAEFFER: J. Amer. chern. Soc. 85, 3592 (1963). 4 HAWTHOR::

Abel, E. W., J. D. Ed• Banus, J. see Beyer, H., J. W. Daw• wards, W. Gerrard Burg, A. B. 57 son, H. Jenne and and M. F. Lappert 38 Barbaras, G. K. see K. Niedenzu 62, 70, -, W. Gerrard, Brown, H. C. 17 101 M. F. Lappert and Barfield, P. A., -, J. B. Hynes, H.Jenne R.Shaffennan 42,43 M. F. Lappert and and K. Niedenzu 90, Abraham, M. A., J. Lee 49 99, 117, 119 J. H. N. Garland, Bartlett, R. K., -, K. Niedenzu and J. H. Hill and H. S. Turner, J. W. Dawson 97, L. F. Larkworthy 34 R.J. Warne, 138, 139, 140 Adams, M. D. see M. A. Young and see Baechle, H. 49, Schaeffer, G. W. 52, W. S. McDonald 120 157 64 see Niedenzu, K. 49, Basile, L. J. see 51, 54, 55, 57, 60, Adams, R. M., and Schaeffer, G. W. 64 F. D. Poholsky 46 67, 69, 70, 77, 79, Battenberg, E. see 99, 104, 129, 130, Anderson, E. R. see Meerwein, H. 29 134, 135, 157 Schaeffer, G. W. 14, Bauer, S. H. 88, 150 see Niith, H. 13, 15, 54, 65, 87, 93, 111 -, G. R. Finlay and 18, 19, 20, 21, 24, Andrews, E. R. see A. W. Laubengayer 29, 37, 38, 41 Zimmer, H. 140 27,29 Bidinosti, D. R. see Apple, E. F. and Beachley jr., o. T. see Laubengayer, A. W. T. Wartik 80 Laubengayer, A. W. 99, 104, 107 Aries R. S. 72 123 Birnbaum, E. R. see Aristorkhova, G. I. see Bean, F. R., and Ryschkewitsch, G. E. Korshak, V. V. 108 J. R. Johnson 46 19 Aronovich, P. M. see Becher, H. J. 32, 49, Bissot, T. C., and Mikhailov, B. M. 66, 50, 51, 57, 72 R. W. Parry 52, 63 96 -, and S. Frick 94, 99, Blau, J. A., W. Gerrard Ashby, E. C. 21 115, 116, 118 and M. F. Lappert 61 -, and W. E. Foster 14 -, W. Nowodny, Blix, F. see Stock, A. - see McCusker, P. A. H. Niith and 153 56 W. Meister 80, 84 Block, F. see Aubrey, D. W., see Baechle, H. 49, McLaughlin, D. E. W. Gerrard and 157 17 E. F. Mooney 71, 72 see Goubeau, J. 10, Blokhina, A. N. see -, and M. F. Lappert 11, 23, 48, 50, 59 Mikhailov, B. M. 66, 97, 119, 125 Becke.Goehring, M., 96, 105, 111 -, - and M. K. Ma• and H. Krill 56 Bloomfield, J. J. see jumdar 71, 72, 73 - and W. Lehr 87 Mulvaney, J. E. 140 -, _. and H. Pyszora Bekasova, N. I. see Boddeker, K. W. see 72 Korshak, V. V. 108 Shore, S. G. 64 Bellamy, L. J., Bohn, U. see Goubeau,J. Baechle, H., H. J. Be• W. Gerrard, 42 cher, H. Beyer, M. F. Lappert and Bolz, A. see Wiberg, E. W. S.Brey, R. L. Williams 42 52, 54, 58, 66, 86, J. W. Dawson, Benson, R. E. see 87, 92, 94, 102, 109, M. E. Fuller II and Holmquist, H. E. 47 118 K. Niedenzu 49, 157 Berzelius, J. J. 35 Boone, J. L., and Balmain, W. H. 2, 153 Besson, A. 35, 40, 41 G. W. Willcockson 108 160 Author Index

Boone, J. L., see Brother• Brotherthon, R. J. Buchheit, P. 52 ton, R. J. 81 A. L. McCloskey, - see Wiberg, E. 52, - see Burg, A. B. 52 J. L. Boone and 54, 58, 64 Bowlus, H., and H. M. Manasevit 81 Buchler, J. W. see J. A. Nieuwland 29, -, - and H. M. Mana• Wiberg, N. 25 :32 sevit 83 Buckman, T. see Bowman, C. M. see -, -, L. L. Pett,: rson Brotherton, R J. 72 Sugihara, J. M. 139 and H. Steinberg 59, Bues, W. see Goubeau, J. Bradford, J. L. see 66, 80, 81, 82 28 Wagner, R 1. 106, -, and H. Steinberg 97, Bundy, F. P. 150 109, II9, 120, 121, 138, 139 Burch, J. E. 123, 125 - see Petterson, L. L. W. Gerrard and Bradley, M. J., 83 E. F. Mooney 67, 69, G. E. Ryschkewitsch Browrr 2 96, 97 and H. H. Sisler 102 Brown, C. A. 139 Burckhardt, R see Brager, A. 148 -, and A. W. Lauben• Hein, F. 44 -, and H. Shdanow 151 gayer 86, 87, 92, 95, Burg, A. B. 30, 63 Brame, E. G., 99, 103, 122 -, and J. Banus 57 L. Muetterties and J. L. Margrave and -, E. -, and J. L. Boone 52 V. M. Meloche 152 E. G. Rochow 29, 30, -, and A. A. Green 10, 32 17, 29, 38 Branch, G. E. K. see -, and R C. Osthoff II, -, and S. Kuljian 53, Yabroff, D. L. 42 E. 17, 58, 71 56 Braun, J. 96 - see Schupp, L. J. 97, -, and L. L. Martin 30 Bray, P. J. see 139 -, and C. L. Randolph Silver, A. H. II4, Brown, E. H. see 54, 66, 71 151 Kraus, C. A. 29, 31, -, and H. 1. Schlesinger Brennan, G. L., 71 37 G. H. Dahl and Brown, H. C. 4, 17 -, and J. P. Slota 67 R Schaeffer 95, 102, -, and G. K. Barbaras -, and J. R Spielman 105 17 27 Brey, W. S., M. E. Ful• -, and E. A. Fletcher see Schlesinger, H. 1. ler II, G. E. Ryschke• 42, 43, 44 16, 17, 21, 22, 24, witsch and -, and M. Gerstein 17 26, 37, 54, 64, 87, A. S. Marshall 49 -, and R. R. Holmes 93, 94, 98, lI8, 120 see Baechle, H. 49, 10, 33 Butcher, 1. M., 157 -, and R B. Johan• W. Gerrard, see Ryschkewitsch, nesen 18 E. F. Mooney, G.E.49 -, and S. Johnson 27, R. A. Rothenburg Brieger, G. see Van 29 and H. A. Willis Tamelen, E. E. 139 -, H. 1. Schlesinger and 116, 117 Bright, J. R, and S.Z.Cardon 17, 29, Buttlar, R 0., W. C. Fernelius 29 31 D. F. Gaines and Brill, R, C. Hermann -, and B. C. Subba Rao R Schaeffer 65 and C. Peters 151 16 Buzzell, A. see Brinckman, F. E., and -, and M. D. Taylor 17 Hoard, J. L. 31, 39 F. G. A. Stone 38 -, - and M. Gerstein Brindley, P. B., 17 W. Gerrard and -, - and S. Sujishi 17 Campbell, G. W., and M. F. Lappert 25 -, and P. A. Tierney 37 L. Johnson 63 Brockway, L. O. see -, and coworkers 18 Cardon, S. Z. see Levy H. 150 Brown, J. F. 24, 53, 54, Brown, H. C. ]7, 29, Brois, S. J. 34 58, 61 31 Brotherton, R J., and Brown, M. P., Carter, J. C. see T. Buckman 72 A. E. Dann, Parry, R W. 26 -, H. M. Manasevit and D. W. Hunt and Cashin, W. N. see A. L. McCloskey 81, H. B. Silver 81, 82 Hoard, J. L. 31 84 -, and H. B. Silver 83 Chalvet, 0., R Daudel -, and A. L. McCloskey Bubnov, Y. A. see and J. J. Kaufman 107 Mikhailov, B. M. 77 90, 114 Author Index 161

Chamberland, B. L. see Dann, A. E., see Ebsworth, E. A. V., and Miller, N. E. 26 Brown, M. P. 81, 82 H. J. Emeleus 56 Champion, N. G. S., Daudel, R. see Eddy, L. B., R. Foster and Chalvet, O. 90, 114 H. S. Smith jr. and R. K. Mackie 113 Davidson, .J. M., and R. R. Miller 88 Chang, S. see Spurr, C. M. French 25 - see Schaeffer, R. 88, R. A. 89, 90 Davies, D. W. 90, 107 98, 103, 121 Chapman, D., Davy, H. 1 Edsall, J. T. see S. H. Glarum and Davy, J. 8, 27 Crawford, B. L. 89, A. G. Massey 118 Dawson, J. K. 152 91 Chissick, S. S., Dawson, J. W. see Edwards, J. D. see M. J. S. Dewar and Baechle, H. 49, 157 Abel, E. W. 38 P. M. Maitlis 138, see Beyer, H. 62, 70, Edwards, J. O. see 141, 145, 146 97, 101, 138, 139, Kelly, H. C. 15, 46 Clarke, P. T., and 140 Ekhoff, E. see H. M. Powell 131 see Fritz, P. 107, Goubeau, J. 42 Cluff, C. L. see 134, 157 Emeleus, H. J., and Taylor, R. C. 23 -- see Niedenzu, K. 49, F. G. A. Stone 16, 76 Coates, G. E. 60, 66, 50, 51, 54, 55, 56, -, and G. J. Videla 95, 71 57, 58, 59, 60, 67, 103 ~, and J. G. Livingstone 69, 70, 75, 77, 79, -, and K. Wade 16, 94 49, 51, 52, 53, 57, 96, 100, 101, 102, - see Ebsworth, 58 105, 106, 109, 110, E. A. V. 56 Coerver, H. J., and 112, 129, 130, 134, Emery, A. R. see C. Curran 39 135 Taylor, R. C. 22 Colclou~h, T., see Wyman, G. IlL English, W. D., W. Gerrard and 50, 51, 56 A. L. McCloskey and M. F. Lappert 42 Deichert, W. G. see H. Steinberg 55, 101 Condike, G. F., and Pellon,.J. 99, 107 - see Newsom, H. C. A. W.Laubengayer28 106 Dewar, IlL J. S. 2, 146 - see Laubengayer, -, and R. Dietz 7, 144, Erickson, C. E., and A. W. 28, 29, 153 14() F. C. Gunderloy 57 Conklin, G. W., and -, -, V. P. Kubba and - see Gunderloy, F. C. R. C. Morris 133 A. R. Lepley 144 60 Coulsen, C. A., -, and R. C. Dougherty Ewers, J. W. see L. B. Redei and 146 Goubeau, J. 42 D. Stocker 151 -, and V. P. Kubba 143 Coursen, D. L., and -, - and R. Pettit Fedotov, N. S. see J. L. Hoard 114 138, 139, 141, 143 Mikhailov, B. M. 25, Cowley, A. H., -, and P. A.Marr 144 69 H. H. Sisler and - see Chissick, S. S. Fenzl, W. see Pailer, M. G. E. Ryschkewitsch 138, 141, 145, 146 134, 140 102 Dewing, 1. 53, 55 Fernelius, W. C. see Coyle, T. D. 38 Bright, J. R. 29 Cragg, R. H., and Dietz, R. see Dewar, Ferris, F. C. see M. F. Lappert 101 M. J. S. 7, 144, 146 Kreutzberger, A. n, -, - and B. P. Tilley Dobrott, R. D. see 12, 13, 29, 30, 32 62, 70, 75 Kaczmarczk", A. Fessenden, R. W. see 35 . Crawford, B. L., and Waugh, J. S. 118 J. T. Edsall 89, 91 Dornow, A. and Finch, A., P. J. Gardner, Curran, C. see Coerver, H. H. Gehrt 71 J. C. Lockhart and H.J.39 Dorochov, W. A. see E .•J. Pearn 74 Mikhailov, B. M. 66 -, and J. C. Lockhart 43 Dahl, G. H., and - see Noth, H. 59, 60, Finlay, G. R. see R. Schaeffer 64, 88, 67, 70 Bauer, S. H. 27, 29 93 Dougherty, R. C. see Fletcher, E. A. see - see Brennan, G. L. 95, Dewar, M. J.S. 146 Brown, H. C. 42, 43, 102, 105 Douglas, A. E., and 44 Dandegaonker, S. H. G. Herzberg 152 Flodin, N. W. see see Letsinger, R. L. 138 Douglas. J. E. 25, 44 Schlesinger, H. 1. 17,37 Niedenzu, Boron-Nitrogen Compounds II 162 Author Index

Foster, R. ll3 Gerrard, W. 4 Goubeau, J., and - see Champion, -, M. Howarth, J. W. Ewers 42 N. G. S. ll3 E. F. Mooney and -, and H. Grabner 62 Foster, W. E. see D. E. Pratt 96 -, and R. Link 42 Ashby, E. C. 14 -, H. R. Hudson and -, and H. Mitschelen Fraser, R. D. B. see E. F. Mooney 100, 28, 29 Price, W. C. 89 101, ll2, 124 -, M. Rahtz and Frazer, J. W. see -, and M. F. Lappert 4, H. J. Becher 10, 11, Pearson, R. K. 94 40 48, 50, 59 French, C. M. see -, - and B. A. Mount• -, and E. Richter 76 Davidson, J. M. 25 field 62 -, and E. Ricker 16 Freyer, W. R. see -, - and C. A. Pearce -, and H. Sclmeider 15 Seyferth, D. 127 10, 11, 36, 55, 58, -, and A. Zappel 25, Frick, S. see Becher,H.J. 59, 61, 67, 71, 73 47, 132, 133, 134, 135 94, 99, ll5, ll6, ll8 -, -, H. Pyszora and - see Ulmschneider, D. Friederich, E., and J. W. Wallis 39 132, 137, 139 V. Sittig 153 -, - and J. W. Wallis Gould, E. S. see Horn Fritz, P. 61, 70 39 H.42 -, K. Niedenzu and -, and E. F. Mooney - see Urs, S. U. 42, 43 J. W. Dawson 107, 12, 29, 36, 105 Gould, J. R. 100 134, 157 -, - and D. E. Pratt Grabner, H. see see Niedenzu, K. 76, 105, llO Goubeau, J. 62 129, 134, 135 see Abel, E. W. 38, 42, 43 Green, A. A. see see Noth, H. 59, 60, Burg,A.B. 10, 17, 67, 68, 69, 70, 71, see Aubrey, D. W. 81, 84 71, 72 29, 38 Fu, H. C., T. Psarras, see Bellamy, L. J. 42 Green, J. H. S., H. Weidmann and see Blau, J. A. 61 W. Kynaston and H. K. Zimmermann see Brindley, P. B. 25 H. M. Paisley 132 45 see ~urch, J. E. 67, Greenwood, N. N., and Fuller II, M. E. see 96, 97 K. Wade 42 Baechle, H. 49, 157 see Butcher, 1. M. Groszos, A., and - see Brey, W. S. 49 ll6, ll7 S. F. Stafiej 99 see Colclough, T. 42 Gunderloy, F. C., and Gaines, D. F., and Gerstein, M. see C. E. Erickson 60 R. Schaeffer 63, 65, Brown, H. C. 17 - see Erickson, C. E. 157 Girardot, P. R. see 57 - see Buttlar, R. O. 65 Parry, R. W. 22 Gustavson, G. 39 Galiano, R. J. see - see Shore, S. G. 22 Gutmann, V., A. Meller Rice, B. 23 Giusto, M. B. see and R. Schlegel 100, Gardner, P. J. see Kelly, H. C. 19 104, 116, 119, 124, Finch, A. 74 Glarum, S. H. see 125 Garland, J. H. N. see Chapman, D. ll8 Gutsche, C. D. see Abraham, M. A. 34 Glemser,O., and Schleppnik, A. A. 46 Garner, P. J. 133 H. Haeseler 153 Gay-Lussac, J. L. 2, Glunz, L. J. see Haeseler, H. see 27, 29 McCusker, P. A. 56 Glemser, O. 153 -, and L. J. Thenard Gmelin 4 1, 8, 27 Gold, H. see Hall, F. R. see Toenikoetter, H. Gehrt, H. H. see Meerwein, H. 29 R. Dornow, A. 71 Goldschmidt, V. M. 152 100, 101, 106, 108, Geller, S., and Gordon, A. J. see ll8, 121, 125 J. L. Hoard 31 Okamato, Y. ll3 Hamann, J. R. see Geller, T. B. see Goubeau, J. 33, 40, 49 Kaufman, J. J. 51, Hoard, J. L. 31 -, and H. J. Becher 23, 146, 147 George, W. see 48, 50 Hamilton, S. B. see Niedenzu, K. 56, 58, -, and U. Bohn 42 Letsinger, R. L. 42, 100, 101, 102 -, W. Bues and 138, 139, 141 Gerrard, J. E. see F. W. Kampmann 28 Harlos, W. see Burch, J. E. 69 -, and E. Ekhoff 42 Pohland, E. 32 Author Index 163

Harrelson;D. H. see Hoard,J.L., S. Geller and Hynes, J. B. see Beyer, Niedenzu, K. 55, 56, T. B. Owen 31 H. 90, 99, 117, Il9 58, 96, 100, 101, -, T. B. Owen, 109, llO, ll2 A. Buzzell and Harrib, J. J. 124 O. N. Salmon 31, 39 Inatome, M., and -, and B. Rudner 104 - see Coursen, D. L. L.P.Kuhn 34 -, and Ph. D. Thesis 114 - see Kuhn, L. P. 35 127 - see Geller, S. 31 Ito, K., H. Watanabe - see Rudner, B. 97, Hoffmann, A. K., and and M. Kubo 91, 139 W. M. Thomas 46 Il7, 118 -. see Ryschkewitsch, Hoffmann, R. 49, 50, - see Watanabe, H. 90, G. E. 96, 99, 100, 105, 51, 65, 142, 143 ll5 Ill, ll2, ll8, 120 Hohnstedt, L. F., and Iwasaki, K. see Hawkins, R. T., D. T. Haworth 88, Koster, R. 55, 61, W. J. Lennarz and 96, 98, 105 73, 75, 136 H. R. Snyder 138 -, and R. F. Leifield 96 -, and H. R. Snyder -, and A. M. Pellicciotto 138, 139 139 Jacobs, L. E., Haworth, D. T., and see Haworth, D. T. J. R. Platt and L. F. Hohnstedt 87, 87, 92, 93, 109, III G. W. Schaeffer 90 92, 93, 109, III see Schaeffer, R. 88, Jenne, H., and - see Hohnstedt, L. F. 98, 103, 121 K. Niedenzu 56, 62, 88, 96, 98, 105, Holle, W. see Stock, A. 74, 75, 97 Hawthorne, M. F. 16, see Beyer, H. 62, 70, 40, 148, 153 17, 18, 19, 21, 53, 90, 99, 101, Il7, ll9 54, 57, 66,69,94,138, Hollerer, G. see Noth, H. 67 seeNiedenzu, K. 49, 139, 157 Holliday, A. 55, 57, 60, 99, 104, -, and E. S. Lewis 19 K., 129, 157 F. J. Marsden and -, and A. R. Pitochelli Joannis, A. 2, 36, 40, 35 A. G. Massey 79, 80 41, 95 -, and A. G. Massey 80 - see Lipscomb, W. N. Johannesen, R. B. see -, - and F. B. Taylor 80 35 Brown, H. C. 18 Heal, H. G. 62 -, and N. R. Thompson Johnson, A. R. 40, 41 Hein, F., and 20 Holmes, R. R. see Johnson, J. R. see Burckhardt 44 R. Brown, H. C. 10, 33 Bean, F. R. 46 Heller, H. H. see Johnson, L. see Camp• Meulen, P. A. van del' Holmquist, H. E., and bell, G. W. 63 29, 31 R. E. Benson 47 Johnson, S. see Brown, Hennion, G. F. see Homberg, G. 1 H. C. 27, 29 McCusker, P. A. 56 Horeld, G. see Wiberg,E. Johnson, W. H. see Hermann, C. see 59, 96, 104 Kilday, M. V. 91 Brill, R. 151 Horn, H., and Jones, R. see Hertwig, K. see E. S. Gould 42 Schaeffer, R. 154 Wiberg, E. ll, 17, Horvitz, L. see Jones, R. G., and 52, 54, 59, 87, 94 Schlesinger, H. 1. 54, C. R. Kinney 36, 71, Herzberg, G. see 87, 94, ll8 95, 105, no Douglas, A. E. 152 Hough, W. V., and Hesse, G., and H. Witte G. W. Schaeffer 53, 47 64 Kaczmarczky, A., Heying, T. L., and Howarth, M. see R. D. Dobrott and H. D. Smith jr. 62 Gerrard, W. 96 W. N. Lipscomb 35 Hickam, C. W. see Hudson, H. R. see Kampmann, F. W. see Shore, S. G. 64 Gerrard, W. 100, Goubeau, J. 28 Hill, J. H. see 101, 112, 124 Kato, S., M. Wada and Abraham, M. A. 34 Hiickel, W. 151 Y. Tsuzuki 135 Hill, L. see Muszkat, Hughes, E. W. 23 Kaufman, J. J., and K. A. 99, 102, 104, Hunt, D. W. see J. R. Hamann 51, 105 Brown, M. P. 81, 82 146, 147 Hoard, J. L., S. Geller Hunter, D. L. see see Chalvet, O. 90, and W. N. Cashin 31 Steinberg, H. 46 Il4 11* 164 Author Index

Kazakova, E. B. see Kraus, C. A., and Lappert, M. F. see Bar• Zhigach, A. F. 94 E. H. Brown 29, 31, field, P. A. 49 Keenan, C. W. see 71 see Bellamy, L. J. 42 McDowel, W. J. 31, 41 Kreutzberger, A., and see Blau, J. A. 61 Kelly, H. C. and F. C. Ferris 11, 12, see Brindley, P. B. 25 J. O. Edwards 15, 46 13, 29, 30, 32 see Colclough, T. 42 -, F. R. Marchelli and Krill, H. see Becke· see Cragg, R. H. 62, M. B. Giusto 19 Goehring, M. 56 70, 75, 101 Kennerly, G. W. see Krongauz, E. S. see see Gerrard, W. 4, Milks, J. E. 48 Zhigach, A. F. 94 10, 11, 36, 39, 40, Kilday, M. V., Kubba, V. P. see 55, 58, 59, 61, 62, W. H. Johnson and Dewar, M. J. S. 138, 67, 71, 73 E. J. Prosen 91 139, 141, 143, 144 Larcombe, B. E., and Killig, K. A. see Kubo,M.51 H. S. Turner 125 Toenikoetter, R. H. see !to,K. 91, 117, Larkworthy, L. F. see 127 118 Abraham, M. A. 34 Kinney, C. R., and see Kuroda, Y. 116 Laubengayer, A. W. 2, M. J. Kolbezen 36, see Nakamura, D. ll4 92, 109, 123 71, 95, 105, 110 see Ohashi, O. 20 -, and O. T. Beachlcy jr. -, and C. L. Mahoney see Totani, T. 49 123 71, 95, llO see Watanabe, H. 89, -, and G. F. Condike 28, - see Jones, R. G. 36, 90, lI5, lI6 29, 153 71, 95, 105, llO Kubo, R. see Suzuki,M. -, P. C. Moews jr. and Kirson, B. see 91 R. F. Porter 91, 122 Muszkat, K. A. 99, Kuhn, L. P., and -, and D. S. Sears 32, 102, 104, 105, 109, M. Inatome 35 39 llO - see Inatome, M. 34 -, K. Watterson, Klevens, H. B. see Kuljian, E. S. see D. R. Bidinosti and Platt, J. R. 90 Burg, A. B. 53, 56 R. F. Porter 99, 103, Kodama, G., and Kurita, Y. see 104, 107 R. W. Parry 27 Ohashi, O. 20 see Bauer, S. H. 27, - see Parry, R. W. 22 Kuroda, Y. see 29 Kogler, H. P. see Watanabe, H. 116 see Brown, C. A. 86, Seyferth, D. 102, Kuss, E. see Stock, A. 21 87, 92, 95, 99, 103, 125 Kynaston, W. see 122 Koenig, F. J. see Green, J. H. S. 132 see Condike, G. F. 28 Schaeffer, G. W. 52, see Moews jr., P. C. 93 64 Lagowski, J. J., and see Weibrecht, W. E. Koster, R. 14, 20, 21 P. G. Thompson 100 93, 109, 110 -, and K. Iwasaki 55, - see Mellon jr., E. K. Lawesson, S. O. 45 61, 73, 75, 136 lI3 Lee, J. see Barfield, Kolbezen, M. J. see Landesman, H., and P.A.49 Kinney, C. R. 36, R. E. Williams 43, Leffler, A. J. 17, 94 71, 95, 105, llO 155 Leffler, J. E., and Konecky, M. S. see - see Onak, T. P. 157 L. J. Todd 78 Snyder, H. R. 30 Landolph, F. 29, 32 Lehmann, W. J. see Kornberg, H. A. see Lang, K., and F. Schu· Rice, B. 23 Snyder, H. R. 29 bert 14 Lehr, W. see Becke· Korshak, V. V., Lappert, M. F. 18, 117, Goehring 87 N. 1. Bekasova, 125 Leifield, R. F. see V. A. Zamyatina -, and M. K. Majumdar Hohnstedt, L. F. 96 and G. 1. Aristorkhova 74, 75, 119, 125, 126 Lennarz, W. J. see 108 -, - and B. Prokai 130 Hawkins, R. T. 138 Koski, W. S. see -, and H. Pyszora 62, - see Snyder, H. R. Ring, M. A. ll5 102, 105, lI2, ll9 30, 142 Kostroma, T. V. see -, and G. Srivastava 75 Lepley, A. R. see Mikhailov, B. M. see Abel, E. W. 38, Dewar, M. J. S. 144 66, 96, 97, 105, III 42,43 Letsinger, R. L. 44 Kozminskaja, T. K. see see Aubrey, D. W. -, and S. H. Dande• Mikhailov, B. M. 96 71,72,73,97,119,125 gaonker 138 Author Index 165

Letsinger, R. L., and Majumdar, M. K. see Meerwein, H., S. B. Hamilton 42, 138, Lappert, M. F. 74, 75, E. Battenberg, 139, 141 119, 125, 126, 130 H. Gold, E. Pfeil and -, and D. B. MacLean Makosza, M. see G;Willfang 29 42 Serafin, B. 42 -, and W. Pannwitz 38 -, and J. R. Nazy 43 Mamantov, G., and Mehrotra, R. C., and -, and N. Remes 43 J. L. Margrave 91 G. Srivastava 42 -, and 1. Skoog 43 Manasevit, H. M. see Meister, W. 84 -, - and N. Remes 43 Brotherton, R. J. 81, see Becher, H. J. 80, Levy, H., and 83, 84 84 L. O. Brockway 150 Marchelli, F. R. see - see N6th, H. 67, 80, Lewis, E. S. see Kelly, H. C. 19 81, 82, 83, 84 Hawthorne, M. F. 19 Margrave, J. L. see Meller, A. 100, 102, 107, Link, R. see Goubeau, J., Brame, E. G. 152 118, 121 42 - see Mamantov, G. 91 -, and R. Schlegel 116 Lippert, E. L., and Markina, V. Y. see - see Gutmann, V. 100, W. N. Lipscomb 23 Mikheeva, V. 1. 87 104, 116, 119, 124, 125 Lipscomb, W. N. 4, 110, Marr, P. A. see Dewar, Mellon jr., E. K., and 154 M. J. S. 144 J. J. Lagowski 113 -, A. R. Pitochelli and Marsden, F. J. see Meloche, V. M. see M. F. Hawthorne 35 Holliday, A. K. 79, Brame, E. G. 152 see Kaczmarczky, A. 80 Meulen, P. A. van der, 35 Marshall, A. S. see and H. H. Heller 29, see Lippert, E. L. 23 Brey, W. S. 49 31 see Trefonas L. M. 63 Martin, L. L. see Meyer, F., and Livingstone, J. G. see Burg, A. B. 31 R. Zappner 148 Coates, G. E. 49, 51, Martini, H. see Michaelis, A., and 52, 53, 57, 58 Stock, A. 87, 103 K. Luxembourg 58, 66 Lloyd, J. E., and Martius, C. A. 35, 39, 95 Michaud, H. see K. Wade 16 Marvel, C. S. see Wiberg, E. 78 Lockhart, J. C. see Mulvaney, J. E. 140 Mikhailov, B. M., and Finch, A. 43, 74 Massey, A. G. see P. M. Aronowich 66, J... onguet-Hig!!:ins, H. C., Chapman, D. 118 96 and L. E. Orgel 128 - see Holliday, A. K. -, A. N. Blokhina and - see Price, W. C. 89 79, 80 T. V. Kostroma 66, Lonsdale, K., and Mathews, F. S. see 96, 105, 111 E. W. Toor 113 Trefonas, L. M. 63 -, and Y. A. Bubnov 77 Lowry, T. M. 9 -, and W. A. Dorochov Lukas, S. see N6th, H. McCloskey, A. L. see 66 58, 59, 67, 72 Brotherton, R. ,T. 59, -, and N. S. Fedotov 69 Luther, H., D. Mootz 66, 80, 81, 82, 83, -, -, T. A. Schegolewa and F. Radwitz 23 84, 107 and W. D. Schelud• see English, W. D. Luxembourg, K. see jakov 25 Michaelis, A. 58, 66 55, 101 -, and T. V. Kostroma see Newsom, H. C. 97, 105 106, 120 Mackie, R. K. see -, and T. K. Kozmins• Champion, N. G. 113 see Woods, W. G. kaja 96 MacLean, D. B. see 104 -, W. D. Schtuljakow Letsinger, R. L. 42 McCusker, P. A., and and T. A. Schtschego• Mahoney, C. L. see L. J. Glunz 56 lewa 59 Kinney, C. R. 71, 95, -, G. F. Hennion and Miheeva, V. 1., and 110 E. C. Ashby 56 V. Y. Markina 87 Maier, G. see Paetzold, McDonald, W. S. see Milks, J. E., G. W. Ken• P.1. 79 Bartlett, R. K. 120 nerly and J. H. Po• Maitlis, P. M. 4, 145 McDowell, W. J., and levy 48 - see Chissick, S. S. C. W. Keenan 3), 41 Miller, F. A., and 138, 141, 145, 146 lHcLaughlin, D. E., C. H. Wilkins 125 Majumdar, M. K. see M. Tamres, Miller, H. C. see Aubrey, D. W. 71, S. Searles jr. and Phillips, W. D. 16, 72, 73 F. Block 17 53, 69, 157 166 Author Index

Miller, M. A. 33 Nakamura, D., H. Wata• Nieuwlaud, J. A. see Miller, N. E., nabe and M. Ku bo Bowlus, H. 29, 32 B. L. Chamberland 114 - see Sowa, F. J. 33 and E. L. Muetter• Narisada, M. see Noth, H. 55, 56, 57, ties 26 Watanabe, H. 116 73, 75, 76, 97, 103, -, and E. L. Muetterties Nazy, J. R. see 129, 134 26 Letsinger, R. L. 43 -, and H. Beyer 13, 15, Miller, R. R. see Nespital, W. 39 18, 19, 20, 21, 24, 29, Eddy, L. B. 88 - see Ulich, H. 39 37, 38, 41, " Mitschelen, H. see -, - and H. J. Vetter Neu, R. 44, 138, 139 Goubeau, J. 28, 29 24 Mixter, W. G. 27, 29 Newsom, H. C., -, W. A. Dorochov, Moews jr., P. C., and W. D. English, P. Fritz and F. Pfab A. W. Laubengayer 93 A. L. McCloskey and 59, 60, 67, 70 - see Lauben- W. G. Woods 106 -, and P. Fritz 59, 60, gayer, A. W. 91, 122 -, W. G. Woods and 67, 68, 69, 71, 81, 84 Mooney, E. F. 117, ll8 A. L. McCloskey -, and G. HoBerer 67 see Aubrey, D. W. 106, 120 -, and S. Lukas 58, 59, 71, 72 Niedenzu, K. 103, 104, 67, 72 see Burch, J. E. 67, 128 -, and W. Meister 67, 69, 96, 97 -, H. Beyer and 80, 81, 82, 83, 84 see Butcher, 1. M. J. W. Dawson 51, 55, -, and W. Regnet 77, 116, ll7 67, 69, 70, 77, 79, 78, 79, 129, 130 see Gerrard, W. 12, 129, 130, 134, 135 -, H. Schick and 29, 36, 96, 100, 101, -, -, - and H. Jenne W. Meister 83 105, llO, ll2, 124 49, 55, 57, 60 -, and G. Schmid 69 Moore, R. E. see Urry, G. -, - and H. Jenne 99, - see Becher, H. J. 80, 79, 80 104, 157 84 Mootz ,D. see Luther, H. 23 -, and J. W. Dawson Nordman, C. E. 27 Morris, R. C. see 49, 50, 57, 58, 59, -, and C. R. Peters 22, Conklin, G. W. 133 60, 100, 102, 105, 23 Mountfield, B. A. see 106, 112 -, and C. Reimann 23 Gerrard, W. 62 -, - and W. George - see Parry, R. W. 26 Muetterties, E. L. 25 101, 102 Nowodny, W. see -, and E. G. Rochow 32 -, P. Fritz and Becher, H. J. 80, 84 see Brown, C. A. 29, J. W. Dawson 76, Nyilas, E., and 30, 32 134, 135 A. H. Soloway 133, - see Miller, N. E. 26 -, W. George and 138, 139 - see Phillips, W. D. J. W. Dawson 100, 16, 53, 69, 157 101 O'Connor, T. E. 148 Mulliken, R. S. 9, 27 -, D. H. Harrelson and - see Thomas jr., J. - see Roothaan, C. C. J. J. W. Dawson 55, 96, 148 90 100, 101, 109, llO Ogg, R. A. 154 Mulvaney, J. E. -, -, W. George and Ohashi,O., Y. Kurita, J. J. Bloomfield and J. W. Dawson 56, 58 T. Totani, H. Wata• C. S. Marvel 140 -, H. Jenne and nabe, T. Nakagawa Musgrave, O. C. 53 P. Fritz 128 and M. Kubo 20 -, and T. O. Park 45 and coworkers 75, see Totani, T. 49 Muszkat, K. A., L. Hill 98, 107, 122 Okamato, Y., and and B; Kirson 99, see Baechle, H. 49, A. J. Gordon 113 102, 104, 105 157 Onak, T. P., -, and B. Kirson 99, see Beyer, H. 62, 70, H. Landesman, 102, 104, 105, 109, 90, 97, 99, 101, 119, R. E. Williams and llO 138, 139, 140 1. Shapiro 157 see Fritz, P. 107, Onyszchuk, M. see Nakagawa, T. see 134, 157 Paterson, W. G. 29, OhaShi, O. 20 see Jenne, H. 56, 62, 32, 33 - see Totani, T. 49 74, 75, 97, Orgel, L. E. see see Watanabe, H. 89, see Wyman, G. M. Longuet-Higgins, ll6 50, 51 56 H. C. 128 Author Index 167

Osthoff, R. C. see Petterson, L. L. see Radwitz, F. see Brown, C. A. 11, 17, Brotherton, R. J. 59, Luther, H. 23 58, 71 66, 80, 81, 82 Rahtz, M. see Owen, T. B. see Pettit, R. see Goubeau, J. 10, 11, Hoard, J. L. 31, 39 Dewar, M. J. S. 138, 48, 50, 59 139, 141, 143 Ramaswamy, K. L. 88 Paetzold, P. I. 78, 109 Pfab, F. see Noth, H. Randolph, C. L. see -, and G. Maier 79 59, 60, 67, 70 Burg, A. B. 54, 66, Pailer, M., and Pfeil, E. see Meer• 71 W. Fenz! 134, no wein, H. 29 Ratajzak, S. 38 Paisley, H. M. see Phillips, W. D., Rector, C. W., Green, J. H. S. 132 H. C. Miller and G. W. Schaeffer and Pannwitz, W. see E. L. Muetterties 16, J. R. Platt 93, 115 Meerwein, H. 38 53, 69, 157 Redei, L. B. see Park, T. O. see PitochelJi, A. R. see Coulsen, C. A. 151 Musgrave, O. C. 45 Hawthorne, M. F. 35 Reedy, A. J. see Parry 2 - see Lipscomb, W. N. Snyder, H. R. 142 Parry, R. W., G. Ko· 35 Regnet, W. see Noth,H. dama and D. R. Platt, J. R., H. B. Kle• 77, 78, 79, 129, 130 Schultz 22 vens and Reimann, C. see -, C. E. Nordman, G. W. Schaeffer 90 Nordman, C. E. 23 J. C. Carter and - see Jacobs, L. E. 90 Remes, N. see G. Terhaar 26 - see Rector, C. W. 93, Letsinger, R. L. 43 -, D. R. Schultz and ll5 Renner, Th. 152, 153 P. R. Girardot 22 Podszus, E. 152 Rice, B., R. J. Galiano see Bissot, T. C. 52, Poggiale, M. 40 and W. J. Lehmann 63 Pohland, E. 40, 41 23 see Kodama, G. 27 -, and W. HarIos 32 Richter, E. see see Schultz, D. R. 22, - see Stock, A. I, 2, Goubeau, J. 76 23 21, 37, 85, 86, 87 Ricker, E. see see Shore, S. G. 22, Poholsky, F. D. see Goubeau, J. 16 23 Adams, R. M. 46 Rideal, S. 27, 29, 95 see Weaver, J. R. 22 Polevy, J. H. see Ring, M. A., and Patein, G. 32 Milks, J. E. 48 W. S. Koski 115 Paterson, W. G., and Porter, R. F. see Ritter, D. M. see M. Onyszchuk 29, 32, Laubengayer, A. W. Schlesinger, H. I. 33 91, 99, 104, 107, 122 21, 64, 87, 93, 98, Pearce, C. A. see Powell, H. M. see 118, 120 Gerrard, W. 10, II, Clarke, P. T. 131 Ritter, W. see 36, 55, 58, 59, 61, 67, Pratt, D. E. see Zimmer, G. 44 71, 73 Gerrard, W. 96, 105 Robinson, T. S. see Pearn, E. J. see - see Mooney, E. F. Price, W. C. 89 Finch, A. 74 llO Rochow, E. G. see Pearson, R. K., and Price, W. C., Brown, C. A. 29, J. W. Frazer 94 R. D. B. Fraser, 30, 32 Pease, R. S. 148, 150, T. S. Robinson and Rojahn, C. A. 44 152 H. C. Longuet-Hig• Romig, R. J. see Pellicciotto, A. M. see gins 89 Snyder, H. R. 29 Hohnstedt, L. F. 139 Prokai, B. see Roothaan, C. C. J., and PelIon, J., W. G. Dei• Lappert, M. F. 130 R. S. Mulliken 90 chert and Prosen, E. J. see Rose 2 W. M. Thomas 99, Kilday, M. V. 91 Rothenbury, R. A. see 107 Psarras, T. see Fu, H. C. Butcher, 1. M. 116, Peters, C. see 45 117 Brill, R. 151 Pyszora, H. see Rudner, B., and Peters, C. R. see Aubrey, D. W. 72 J. J. Harris 97, 139 Nordman, C. E. 22, see Lappert, M. F. - see Harris, J. J. 104 23 62, 102, 105, 112, Ruff, J. K. 53, 56, 57, Petterson, L. L., and 119 66, 69, 157 R. .T. Brotherton 83 see Wallis, J. W. 39 Ryschkewitsch, G. E. 19 168 Author Index

Ryschkewitsch, G. E. and Schlegel, R. see Seyferth, D., and E. R. Birnbaum 19 Gutmann, V. 100, M. Takamizawa 107 -, W. S. Brey and 116, 124, 125 Shafferman, R. see A. Saji 49 - see Meller, A. 104, Abel, E. W. 42, 43 -, J. J. Harris and 116, 1I9 Shapiro, I. see H. H. Sisler 96, 99, Schleppnik, A. A., and Onak, T. P. 157 100, 105, lIl, 112, C. D. Gutsche 46 Shdanow, H. see 118, 120 Schlesinger, H. I. 2 Brager, A. 151 see Bradley, M. J. 102 -, and A. B. Burg 16, Sheldon, J. C., and see Brey, W. S. 49 22, 24, 26 B:C. Smith 88 see Cowley, A. H. 102 -, N. W. Flodin and A. B. Burg 17, 37 Shoolery, J. N. 154 Saji, A. see Ryschke• -, L. Horvitz and - see Schaeffer, R. 154 witsch, G. E. 49 A. B. Burg 54, 87, Shore, S. G., Saint-Claire Devilla, H. 94, 118 P. R. Girardot and see Wohler, F. 1 -, D. M. Ritter and R. W. Parry 22 Salmon, O. N. see A. B. Burg 21, 64, 87, -, and C. W. Hickam 64 Hoard, J. L. 31, 39 93, 98, lI8, 120 -, - and K. W. Bod- Samsonov, G. V., and see Brown, H. C. 17, deker 64 V. M. Sleptsov 150 29, 31 -, and R. W. Parry 22, Schaeffer, G. W., see Burg, A. B. 37 23 M. D. Adams and see Schaeffer, G. W. - see Weaver, J. R. 22 F. J. Koenig 52, 64 87, 93 Sidgwick, N. V. 9 -, and E. R. Anderson see Schaeffer, R. 88, Sill, A. D. see 14, 54, 65, 87, 93, 98, 103, 121 Zimmer, H. 140 111 see Steindler, M. J. Silver, A. H., and -, and L. J. Basile 64 16, 76 P. J. Bray 114, 151 -, R. Schaeffer and see Urry, G. 79, 80 Silver, H. B. see H. I. Schlesinger 87, Schmid, G. see Noth, H. Brown, M. P. 81, 93 69 82, 83 see Hough, W. V. 53, Schneider, H. see Sisler, H. H. see 64 Goubeau, J. 15 Bradley, M. J. 102 see Jacobs, L. E. 90 Schtschegolewa, T. A. - see Cowley, A. H. see Platt, J. R. 90 see Mikhailov, B. M. 102 see Rector, C. W. 93, 59 see Ryschkewitsch, 115 Schtuljakow, W. D. see G. E. 96, 99, 100, Schaeffer, R. 63 MikhaiIov, B. M. 59 ]05, 11], 112, 118, -, J. N. Shoolery and Schubert, F. see 120 R. Jones 154 Lang, K. 14 Sittig. V. see Fried• -, M. Steindler, Schultz, D. R., and rich, E. 153 L. F. Hohnstedt, R. W. Parry 22, 23 Skinner H. A., and H. S. Smith jr., - see Parry, R. W. 22 N. B. Smith 60, 66, L. B. Eddy and - see Taylor, R. C. 22 71,72 H. I. Schlesinger 88, Schupp, L. J., and Skoog, I. see Let• 98, 103, 121 C. A. Brown 97, 139 singer, R. L. 43 see Brennan, G. L. Schuster, K. see Sleptsov, V. M. see 95, 102, 105 Wiberg, E. 52, 58, Samsonov, G. V. 150 - see Buttlar, R. O. 65, 66, 71, 72 Slota, J. P. see see Dahl, G. H. 64, Searles jr., S. see Burg, A. B. 67 88,93 McLaughlin, D. E. 17 Smalley, J. H., and see Gaines, D. F. 63, Sears, D. S. see S. F. Stafiej 98, 99, 65, 157 Laubengayer, A. W. 118, 120 see Schaeffer, G. W. 32, 39 Smith, B. C. see 87, 93 Serafin, B., and Sheldon, J. C. 88 Schegolewa, T. A. see M. Makosza 42 Smith jr., H. D. see MikhaiIov, B. M. 25 Seyferth, D., Heying, T. L. 62 Scheludjakov, W. D. see W. R. Freyer and Smith jr., H. S. see MikhaiIov, B. M. 25 M. Takamizawa 127 Eddy, L. B. 88 Schick, H. see Noth, H. -, and H. P. Kogler see Schaeffer, R. 88, 83 102, 125 98, 103, 121 Author Index 169

Smith, N. B. see Sturm W. see Wiberg, E. Tomaschek, H. see Skinner, H. A. 60, 66, 71 Tiede, H. 148 66, 71, 72 Subba Roo, B. C. see Toor, E. W. see Snyder, H. R., Brown, H. C. 16 Lonsdale, K. 1I3 M. S. Konecky, and Siitterlin, W. see Totani, T., H. Wata• W. J. Lennarz 30 Wiberg, E. 36, 38, 58 nabe, T. Nakagawa, -, H. A. Kornberg and Sugden, S., and O. Ohashi and R. J. Romig 29 M. Waloff 29 M.Kubo 49 -, A. J. Reedy and Sugihara, J. M., and see Ohashi, O. 20 W. J. Lennarz 142 C.M. Bowman 139 see Watanabe, H. 89 -, and C. Weaver 42 Sujishi, S., and S. Witz Trefonas, L. M., and - see Hawkins, R. T. 56, 104 W. N. Lipscomb 63 138, 139 - see Brown, H. C. 17 -, F. S. Mathews and Soloway, A. H. 146 Suzuki, M., and R. Kubo W. N. Lipscomb 63 - see Nyilas, E. 133, 91 Tsuzuki, Y. see Kato, S. 138, 139 135 Sowa, F. J., and Taft, R. W. 17 Turner, H. S. 102 J. A. Nieuwland 33 Takamizawa, M. see -, and R. J. Warne 96, Spielman, J. R. see Seyferth, D. 107,127 105, 131, 132 Burg, A. B. 27 Tamres, M. see see Bartlett, R. K. Spurr, R. A., and McLaughlin, D. E. 17 120 S. Chang 89, 90 Taylor, F. B. see see Larcombe, B. E. Srivastava, G. see Holliday, A. K. 80 125 Lappert, M. F. 75 Taylor, M. D. see - see Mehrotra, R. C. Brown, H. C. 17 Ulich, H., and 42 Taylor, R. C. 20 W. Nespital 39 Stafiej, S. F. see -, and C. L. Cluff 23 Ulmschneider, and Groszos, A. 99 D., -, D. R. Schultz and J. Goubeau 132, 137, - see Smalley, J. H. A. R. Emery 22 139 98, 99, ll8, 120 Terhaar, G. see Untch, K. G. see Steinberg, H., and Parry, R. W. 26 Van Tamelen, E. E. D. L. Hunter 46 Thenard, L. J. see 139 see Brotherton, R. J. Gay.Lussac, J. L. 1, Urry, G., T. Wartik, 59, 66, 80, 81, 82, 8, 27, 29 R. E. Moore and 97, 138, 139 Thesis, Ph. D. see see English, W. D. H. I. Schlesinger 79, Harris, J. J. 127 80 55, 101 Thomas jr., J., Urs, S. U., and Steindler, M. J. see N. E. Weston and E. S. Gould 42, 43 see Schaeffer, R. T. E. O'Connor 148 98, 103, 121 Thomas, W. M. see -, and H. J. Schle- Hoffmann, A. K. 46 Van Tarnelen, E. E., singer 16, 76 - see PelIon, J. 99, 107 G. Brieger and - see Schaeffer, R. 88 Thompson, N. R. see K. G. Untch 139 Stock, A. I, 40, 121 Holliday, A. K. 20 Vetter, H. J. see -, and F. Blix 153 Thompson, P. G. see Noth, H. 24 -, and W. Holle 40, Lagowski, J. J. 100 Videla, G. J. see 148, 153 Tiede, H., and Erneleus, H. J. 95, -, and E. Kuss 21 H. Tomaschek 148 103 -, and E. Pohland I, Tierney, P. A. see 2, 21, 37, 85, 86, 87 Brown, H. C. 37 'Wada, M. see Kato, S. -, E. Wiberg and Tilley, B. P. see 135 H. Martini 87, 103 Cragg, R. H. 62, 70, Wade, K. see Erne• -, and R. Wierl 88 75 leus, H. J. 16, 94 Stocker, D. see Todd, L. J. see Leffler, - see Greenwood, Coulsen, C. A. 151 J.E.78 N.N.42 Stone, F. G. A. 4 Toeniskoetter, R. H., - see Lloyd, J. E. 16 - see Brinckman, F. E. and F. R. Hall 100, Wagner, R. I., and 38 101, 106, 108, 118, J. L. Bradford 106, - see Emeleus, H. J. 121, 125 109, ll9, 120, 121, 16, 76 -, and K. A. Killig 127 123, 125 170 Author Index

Wallis, J. W. see Weidmarm. H. see Fu, H. Willis, H. A. see But• Gerrard, W. 39 C.45 cher, I. M. 116, 117 Waloff, M. see Weintraub, G. 153 Witte, H. see Hesse, G. Sugden, S. 29 Wentorf, R. H. 150 47 Warne, R. J. see Weston, N. E. see Witz, S. see Sujishi, S. Bartlett, R. K. 120 Thomas jr., J. 148 56, 104 - see Turner, H. S. 96, White, D. G. 135, 144 Wohler, F. 2, 152 105, 131, 132 Wiberg, E. 3, 4, 21, 48, -, and H. Saint-Claire Wartik, T. see 49, 63, 92 Deville I Apple, E. F. 80 -, and A. Bolz 66, 86, Woods, W. G., and - see Urry, G. 79, 80 87, 92, 102, 109, A. L. McCloskey 104 Watanabe, H., K. Ito 118 - see Newsom,H. C. and M. Kubo 90, -, - and P. Buchheit 106, 120 115 52, 54, 58 Wyman, G. M., K. Nie• -, and M. Kubo 89 -, and P. Buchheit 64 denzu and -, Y. Kuroda and -, and K. Hertwig 11, J. W. Dawson 50, M.Kubo 116 17, 52, 59, 94 51, 56 -, M. Narisada, -, - and A. Bolz 54, T. Nakagawa and 87, 94 M. Kubo 116 -, and G. Horeld 59, Yabroff, D. L., and -, T. Totani, T. Naka· 96, 104 G. E. K. Branch 42 gawa and M. Kubo 89 -, and H. Michaud 78 Young, M. A. see see Ito, K. 91, 117, -, and K. Schuster 52, Bartlett, R. K. 120 118 58, 66, 71, 73 see Nakamura, D. -, and W. Sturm 66, 71 114 -, and W. Siitterlin 36, Zamyatina, V. A. see see Ohashi, O. 20 38, 58 Korshak, V. V. 108 see Totani, T. 49 -, see St.ock, A. 87, 103 Zappel, A. see Watterson, K. see Wiberg, N., and Goubeau, J. 25, 47 Laubengayer, A. W. J. W. Buchler 25 132, 133, 134, 135 99, 104, 107 Wierl, R. see Stock, A. Zappner, R. see Waugh, J. S., and 88 Meyer, F. 148 R. W. Fessenden 118 Wiesboeck, R. A. 35 Zhigach, A. F., Weaver, C. see . Wilkins, C. H. see E. B. Kazakova and Snyder, H. R. 42 Miller, F. A. 152 E. S. Krongauz 94 Weaver, J. R., Willcockson, G. W. see Zimmer, G., and S. G. Shore and Boone, J. L. 108 W. Ritter 44 R. W. Parry 22 Willfang, G. see Meer• Zimmer, H., Weibrecht, W. E. 109, wein, H. 29 A. D. Sill and 110 Williams, R. E. see E. R. Andrews 140 -, and A. W. Lauben• Landesman, H. 43, Zimmermann, H. K. 44, gayer 93, 109, no 155 45 Weidmarm, H., and - see Onak, T. P. 157 see Fu, H. C. 45 H. K. Zimmermann Williams, R. L. see see Weidmann, H. 44, 45, 138 Bellamy, L. J. 42 44, 45, 138 Subject Index Bold-face type denotes reference(s) of major import acetamide-trifluoroborane 33 ammonia I, 14, 17, 21, 26, 27, 35, 36, acetonitrile-trifluoroborane 16 37, 40, 41, 64, 80, 85, 87, 94, 97, acetonitrile-trichloroborane 39 98, 100, 122, 131, 148 acetonitrile-trifluoroborane 32, 41 ammonia-borane 21, 23 alkoxyboranes 14, 25, 42, 43, 61, 67, ammonia-chloroborane 37 72, 81, 92, 97, 155 ammonia-dimethylchloroborane 11 B-alkoxyborazines 92, 101, II 7, 119, 125 ammonia-triborane 23 alkylamine-trifluoroboranes 28, 30, 104 ammonia-triethylborane 94 alkylamine-trimethylboranes 17, 133 ammonia-trifluoroborane 2, 8, 20, 27, alkylmercaptoboranes 21, 77 28, 30, 153 amine-alkoxyboranes 38, 42-46 ammonia-trimethylborane 20, 37, 54 amine-boranes 3, 5, 8-48, 54, 58, 66, ammonia-trimethoxyborane 92 68,77,94,131,133,135,136,138,156 ammonium :fluoroborate 28, 33, 104, 153 bond nature 8, 30, 34, 39, 41, 42, ammonium hydroborate 22 45,46 aniline-trichloroborane 36 classification 3 aniline-trifluoroborane 13, 29 preparation 8, 14, 26, 37 aniline-trimethylborane 94 preparative examples 18, 40 aryloxyboranes 42 amine-halogenoboranes 12, 20, 24, 27, 1,2-azaboracycloalkanes 135, 136 35, 37, 38, 54, 74, 131 1,2-azaboracyclohexane 144 amine-arganoboranes 14-21, 37, 94 azidoboranes 78 amine-arganohalogenoboro,nes 38 azidoborazines 102, 105 amine-trichloroboranes 10,11,24,35,131 azidochloroborane 78 amine-trifluoroboranes 27, 37, 41, 104, azidodimesitylborane 78 158 aminoalcohols 33, 43, 44 1,3,2-benzodiazaborolidines 97, 132, aminoalkoxyboranes 61, 67 137-141 aminoborane 52, 64, 65, 86 1,3,2-benzodiheteroborolidines 138, 139 aminoboranes 8,13,20,48-84,97,133, benzonitrile-trifluoroborane 32 135, 136, 137, 138 biborazinyl-see diborazinyl, boraza- bond nature 48 biphenyl classification 3 biguanidine 47 dimers 52, 57 (bisamino)alkoxyboranes 67 heterocycles 47, 133 bisaminoboranes 59, 66-71, 73, 74,77, preparative examples 58, 61, 70, 73, 96, 97, 98, 129, 130, 134, 137 79, 84 bisaminoboranes 61, 67, 80 trimers 52, 62 bisborolanes 55, 61, 73 polymers 53 bis(t-butylamino)chloroborane 74 B-aminoborazines 91, 100, 104, 106, bis(dialkoxy)halogenoboranes 61 117, 119, 124, 125, 126 bis(dialkylamino)halogenoboranes 61 aminoborolanes 55, 61, 73 bis(di-t-butylaminoboryl)-t-butylamine aminodialkoxyboranes 61 128 aminodiisocyanatoborane 62 bis(diethylamino)azidoborane 79 aminodifluoroborane 30 bis(dimethylamino)borane 66, 67, 70, aminodimethylborane 11, 52, 54, 120 83 aminodiphenylborane 52 bis(dimethylamino )bromoborane 66 aminohalogenoboranes 54, 57, 58, 61, bis(dimethylamino)butylborane 68 67, 74, 81, 83, 84, 131 bis(dimethylamino)chloroborane 66,70, aminomercaptylboranes 66, 97 71 172 Subject Index

1,2-bis( dimethylamino )-1 ,2-dichloro• butylamine-halogenoboranes 38 diborane(4) 80, 83 t-butylamine-trifluoroborane 28 bis(dimethylamino)methylborane 68,71 butylamine-trimethylborane 17 bis(dimethylamino)phenylborane 70, t-butylborane 16 129, 130 bis(N,N-dimethylhydrazino)phenyl- carbon monoxide-borane 26 borane 79 bishydrazinoboranes 77 charge-transfer complexes 113 chloroborane 24, 25, 37, 38 bis(methylamino)bromoborane 40 2-chloroborazine 123 bis(thioureido)borane 70 2-chloro-4,6-difluoroborazine 99 bis(trimethylsilyl)amine 56, 73, 74, 97 1-chloro-1,3,2-dioxoborolidine 75 bond distances 23, 25, 30, 63, 85, 86, 88, 91, 114, 150 2-bora-1,3-diazaazulenes 47 decaborane no borazabiphenyl 91, 122, 123 decahydrodecaborate 35 borazanaphthalene 91, 122, 123 dialkylamine-trichloroboranes 24 2,1-borazarenes 7, 136, 143 dialkylchloroboranes 73 4,1-borazarenes 145 diamines 12, 13, 14, 15, 31, 32, 47, 80, 10,9-borazaroanthracenes 145 97, 133 borazaromatics 7, 142 2,4-diaminoborazine 91, 122 2,1-borazaronaphthalene 7, 144 1,2-diaminodiboranes(4) 81 9,10-borazaronaphthalene 146 diammoniate of diborane 2, 21, 64, 86 12,11-borazarophenanthrene 146 1,3,2-diazaboraazulenes 47 borazaro-i-quinoline 146 1,3,2-diazaboracycloalkanes 134 borazine I, 2, 6, 85--93, 98, 102, 117, 1,3,2-diazaboracyclopentane 6 122, 124, 155 diazaboretane-see s-diazadiborine borazines 3, 6, 7, 8, 16, 20, 62, 64, 72, 1,3,2-diazaborolidine 6 85-126, 136, 140 diazaboroline 6 adducts 63, 64,92,93, 109, 110, 113, s-diazadiborines 78, 127 123 diazomethane 102 classification 3 1,3,2-diboraazacycloalkanes 136 physical chemistry 113 1,3-dibora-2,4-diazanaphthalene 137 polynucleated 91, 100, 121 2,7-dibora-1,8-diazaroanthracene 145 properties and reactions 93, 98, 102, 4,10-dibora-5,9-diazaropyrene 145 122, 123 2,5-diboradihydropiperazine 47 unsymmetrically substituted 99, 106, diborane 1, 4, 8, 14, 15, 16, 21, 64, 85, 118 93, 94, 130 borazole-see borazine diborane(4) 79 borazylammonium salts 24, 26, 59, 67, 2,5-diborapiperazine 79 68, 69, 72, 77, 87, 130 (see also diborazinyls 91, 108, 122, 123, 124 boronium salts) diborylamines 73, 128, 129 borazyl oxides 126 diborylhydrazines 76 borolanes 55, 61, 73, 74 2,4-dibromoborazine 92, 98, 102, ll8 boron 1, 2, 42, 116, 154, 157 dibutylamine-borane 15 boronides 48 (di -n-butylamino )dichloroborane 53 boronium salts 12, 15, 19, 22, 24 (see 2,4-di-n-butyl-6-chloroborazine 121 also borazylammonium salts) 2,4-dichloro-6-fluoroborazine 99 boron nitride 2, 4, 28, 33, 147 dichlorophenylborane-see phenyl- boron-nitrogen compounds dichloroborane classification 3, 127 2,4-dichloro-1 ,3,5 ,6-tetraethylborazine historical dates 1, 2, 132 121 nomenclature 5, 44, 45, 63, 79, 127, 2,4-dichloro-N-trimethylborazine 119 129 di(1,3,2-dioxoborolidyl)amine 75 boroxazolidines 44 diethylamine-borane 15 boroxines 17, 18, 31, 55, 66, 80, 107, diethylamine-tribromoborane 40 138, 145 diethylamine-trichloroborane 11, 13 p-bromoaniline-trichloroborane 36 diethylamine-trifluoroborane 28 bromoborane 38 diethylamine-trimethylborane 17 IX-bromo-2 -tolyl-dihydroxyborane 142 (diethylamino)dichloroborane 53, 58 butylamine-borane 15 (diethylamino )diethylborane 58 Subject Index 173

1,:~,2-diheteronorolidines 6, 75, 76, 97, hexamethylborazine 59, 94, 106, 113, 138, 139 116 dimesitylfluoroborane 78 hexaphenylborazine 78, 106 N-dimethylallylamine 46 hydrazine 16, 33, 42, 76, 77, 80, 96, 100, dimethylamine-borane 15, 54 129, 130 dimethylamine-halogenoboranss 38 hydrazine-borane 16, 76 dimethylamine-tribromoborane 40 hydrazinoboranes 76, 129 dimethylamino-trichloroborane 10, II, hydrazinodiphenylborane 78 12, 61 hydroboration 21 dimethylamine-trimethylborane 17, 54 hydrogen cyanide 32, 39, 41, 80 dimethylaminoborane 52, 53, 54, 55, hydroxyboranes 18, 35, 42 63, 66 hydroxylamine 33, 3b, 42, 96 dimethylaminoboron 83 (dimethylamino)butylborane 83 infrared data (dimethylamino )dibromoborane 53 amine-boranes II, 12, 13, 15, 20, 23, (dimethylamino)dichloroborane II, 52, 24, 28, 34, 35, 39, 42, 45, 48 53, 60, 61, 71 aminoboranes 47, 50, 51, 53, 68, 72, (dimethylamino)dimethylborane 5, 54, 80, 84, 135 80 azidobranes 78 (dimethylamino )methylborane 52 bisaminoboranes 68 (dimethylamino )methylfluoroborane 59 borazines 89, 90, 115, 122 N ,N-dimethy laniline- trichloroborane 36 borazylammonium salts 24, 68 N,N-dimethylaniline-trifluoroborane 29 boroxazolidines 45 1,6-diboracyclodecane 6 boron nitride 152 dimethylchloroborane II tetrazadiborines 129, 130 dimethylfluoroborane 57, 59 tetrazadiborines 129, 130 (N,N -dimethylhydrazino)dibutylborane iodoborane 38 79 B-isocyanatoborazines 119 (N,N-dimethylhydrazino(diphenyl- isocyanatodimethylborane 62 borane 77 o,N -dimethylhydroxylamine- borane 63 N-lithioborazines 109, 120, 123 2,4-dimethyl-N- trimethylborazine II9 lithiumhydro borate 9, 14, 18, 54, 88, 93 (di-n-pentylamino)di-n-pnetylborane 58 di-n-pentylchloroborane 58 mercaptylboranes 21 diphenylamine-trichloroborane 36 methoxydimethylborane 5 (diphenylamino)diphenylborane 51, 58 methylamine-borane 15, 63 diphenylchloroborane 25 methylamine-bromoborane 38 dipole moments 19, 20, 32, 49, 88, 89, methylamine-chloroborane 5, 38 131, 143, 150 methylamine-iodoborane 38 dipropylamine-borane 15 methylamine-trifluoroborane 30 disilylaminoborane 52 methylamine-trimethylborane 17 disproportionation 4,55,56,57,59,66,70 methylaminoborane 52, 63, 65 (methylamino)dimethylborane 52 ethylamine-borane 15 (methylamino)diphenylborane 52 ethylamine-trifluoroborane 28 (methylamino)methylchloroborane 59 ethylamine-trimethylborane 17 (methylamino)methylfluoroborane 59 (ethylamino)dibromoborane 40 methylborane 5 ethylenediamine 15, 31, 47, 80, 133 methyldiborane 54, 94 ethyleneimine-trimethylborane 17 methyldibromoborane 83 ethylene oxide 102 N -methylethyleneimine-trimethyl- borane 17 fluoroalkylborazines 94 I-methyl-B-trimethylborazine 121 B-fluoroborazines 99, 103, 107, 108 2-methyl-N-triphenylborazine 120 molecular orbital calculations 49, 50, heptasulfur imide 62 51, 90, 114, 142, 146, 147, 151 heteroaromatics 2, 142 morpholinodichloroborane 53 heterocyclic boron compounds 6, 7, 16, 25, 35, 42-48, 52, 55, 57, 61, nomenclature 5, 44, 45, 63, 79, 127, 129 63-65, 77, 78,85-126,126-132, nitrides 149 132--147 nitriles 16, 30, 32, 39, 41, 93 174 Subject Index nitrogen oxides 33 J,2,4,5-tetraphenyl-2,3,4,1-triaza- nuclear magnetic resonance data boracyclopentene 78 boron-II 15, 42, 48, 63, 69, 91, 151, 1,2,4,5-tetraza-3,6-diborines 129 154-157 8-tetrazatetraborines 130 proton 20, 49, 50, 65, 91, 117, 118 transamination 4, 55, 56, 71, 77, 81, 100 oxyboranes 18, 35, 38, 42-48, 61, 66, trialkoxyboranes 14, 42, 43, 72, 97 72, 81, 97, 101, 119 tolylamine-trichloroborane 36 transboronation 55 pentamethylborazine 119 trialkylamine-boranes 20, 21 pentamethyl-6-chloroborazine 119 trialkylboranes 14, 16, 21, 34, 47, 55, (phenylamino )diethylborane 137 77, 84 2-pnenyl-l,2-azaboracyclohexane 136 B-triaminoborazine 100 2-phenyl-2-boradihydroperimidine 141 B-triaminoborazines 100, 101, 104, 106 2-phenyl-2,1-borazarene 136, 144 l,8,lO,9-triazaboradecalin 135 phenyldichloroborane 25, 70, 129, 130 l,3,4-triaza-2,5-diborines 128 phenyl isonitrile 47 B-triazidoborazine 105 phosphorylated borazines 102, 104 8-triazatriborine-see borazine piperidine-trifluoroborane 28 triborylamines 76 piperidinoboranes 62 tribromoborane 38, 40, 62, 66, 69, 71, piperiodinodichloroborane 53 83, 96, 148, 155 polyamine-trifluoroboranes 31 B-tribromoborazines 103, 105, ll8 potassium aminotrimethylborate 20 tri-n-butylamine-borane 15 propylamine-borane 15 trichloroacetonitrile-borane 16 propylamine-trimethylborane 17 trichloroborane 5, 11, 25, 35, 38, 39, i-propylaminoborane 53 57, 61, 62, 70, 78, 83, 88, 92, 95, 96, pseudohalogenoborazines 102, 105, 119, 97, 101, 114, 139, 155 120 B-trichloroborazine 2, 4, 7, 88, 92, 95, pyridine-azidodiphenylborane 78 96, 98, 99, 100, 102, 103, 104, 107, pyridine-borane 19 113, 115, 116, 117, 119 pyridine-cbloroborane 24, 38 B-trichloroborazines 89, 96, 99,100,101, pyridine-phenylborane 19, 25 102, 104, 105, 106, 108, 109, 111, pyridine-trichloroborane 40 116, 117, 119, 120 pyridine-trifluoroborane 28, 30, 31 B-tricyanoborazine 105 N-trideuteroborazine 89 Raman spectra 84, 89, 115, 135 triethoxyborane 43, 92 triethylamine-borane 15, 137 slloxyborazines 102 triethylamine-chloroborane 38 silylborazines 102 triethylamine-trichloroborane 11, 36 sodium hydroborate 6, 14, 15, 16, 20, triethylamine-trifluoroborane 28, 38 22, 64, 88, 93, 98, 157 triethylamine-trimethylborane 17 sodium hydride 20 B-triethylborazine 94 sodium methyltrihydroborate 6 N-triethylborazine 94 sodium tetraphenylborate 26, 48 B-triethyl-N-trimethylborazine 112 trifluoroborane 13, 25, 27, 33, 35, 37, tables-listing see end of index 38, 57, 71, 96, 153, 155 tetraalkyldiborane 16, 55, 61, 74, 76, 136 B-trifluoroborazine 99, 103, 107, 108 tetraalkyldiboranes(4) 80 B-trifluoroborazines 96, 104 tetrachlorodiborane(4) 83 B-trifluoroboroxine 107 B-tetrachloro-N-tetra-t-butyl-tetraza- trihalogenoboranes 2, 4, 12, 14, 25, 27, tetraborine 132 37, 38, 55, 66, 83, 95 tetrafluorodiborane( 4) 83 B-trihydroxyborazine 92 tetrakisalkoxydiboranes(4) 81 triiodoborane 25, 40, 96 tetrakisaminodiboranes(4) 80, 82, 124 B-triodoborazines 103, 105 tetrakis(dimethylamino)diborane(4) 80, B-triisocyanatoborazines 105 81, 83, 84 trimethoxyborane 42, 92, 115 1,2,4,6-tetramethylborazine 121 B-trimethoxyborazine 100, 109, 113 tetraphenylethylene 50 B-trimethoxy-N-triethylborazine 112 2,3,4,6-tetraphenyl-l ,3,2 -oxazaborole trimethylamine-alkylboranes 18, 66 141 trimethylamine-azidoborane 26 Subject Index 175 trimethylamine-borane 9, 10, 15, 16, trisaminoboranes 55, 59, 66, 69, 71, 77, 26, 37, 46, 57, 66, 93 97, 125, 135, 140 trimethylamine-bromoborane 38 trisazidoborane 78 trimethylamine-chloroborane 37 B-tri(t-butoxy)-N-trimethylborazine trimethylamine-dibromoborane 38 125 trimethylamine-dimethylfluoroborane tris(t-butylamino)borane 128 10,38 B-tris(dialkylamino) borazines 124 trimethylamine-iodoborane 38 B-tris(dibutylamino )borazine 112 trimethyl(N,B)-(methylamino)methyl• tris(diethylamino)borane 73 borane 6 B-tris(diethylamino)borazine 101 trimethylamine-methyldifluoroborane B-tris( diethylamino )-N- triethylborazine 10 101, 119 trimethylamine-phenylborane 136 tris(dimethylamino)alane 55, 66 trimethylamine-tribromoborane 41 tris(dimethylamino)borane 5, 61, 62, trimethylamine-trichloroborane 10, 36, 69, 70, 71, 72, 80, 83, 140 83 B-tris(dimethylamino)borazine 112 trimethylamine-fluoroborane 5, 9, 10, B-tris(N,N-dimethylhydrazino)-N-tri- 28,30 ethylborazine 112 trimethylamine-trimethylborane 10, 17 tris(ethanolamine- borane) borate 46 trimethylborane 11, 37, 47, 57, 94, 98, B-trishydrazinoborazine 100 133, 138, 154 B-tris( isocyanato )-N- tri -n-propyl• B-trimethylborazine 94, 115, 120 borazine 112 N-trimethylborazine 63, 65,93, 98, 111, B-tris(methylamino)-N-triphenyl- 117 borazine 108 B-trimethyl-N-lithioborazine 120 tris(methylamino)borane 73 B-trimethyI-N - trimethylborazine-see tris(phenylamino)borane 71, 72 hexamethylborazine B-trisureidoborazines 101 B-trimethyl-N-triphenylborazine 94, B-tri-p-tolylborazine III 106, 115 B-trivinylborazine 107 B-triphenylborazine 100, 106, 113 B-trivinyl-N-triphenylborazine 107 B-triphenyl-N-triethylborazine 118 B-triphenyl-N-triphenylborazine-see ultraviolet spectra 90, 113, 115, lI8, hexaphenylborazine 141, 143 B-triphenyl-N-trimethylborazine 106 urea-trifluoroborane 32 tri-n-propylamine-borane 10 ureidoboranes 62 Table Index

Historical dates of boron-nitrogen chem• Tetrakisaminodiboranes(4) 82 istry 2 Physical constants of borazine and ben• Elemental characteristics of boron, car• zene 85 bon and nitrogen 2 Bond distances in borazine and benzene Alkylamine-boranes derived from BH3 86 15 Influence of pressure in the borazine Alkylamine-trimethylboranes 17 synthesis 87 Dipole moments of some alkylamine• Assignment of fundamentals of borazine boranes 20 89 Comparison of lIBN in isotopic derivat• B-Trihalogenoborazines 103 ives of ammonia-borana 23 B-Trifluoroborazines 104 Adducts of trifluoroborane with amines B-Trichloroborazines 105 28 B-Tribromoborazines 105 Dissociation of pyridine-trifluoroborane B-Triiodoborazines 105 29 B-Tripseudohalogenoborazines 105 Bond distances in some amine-trifluoro• Thermal stability of substituted bor- boranes 30 azines 106 Diamine adducts with two BF3 molecules B-N Absorption of borazines 115 32 Major infrared absorptions of B-tri• BOl3 Addition compounds with amines 36 chloroborazine 116 Amine-monohalogenoboranes 38 B-N Absorption of borazines 117 RCN Adducts of trifluoroborane and Chemical shift data of single protons in tribromoborane 41 borazines 117 B-N Stretching bands of amino• Electronegativity of nitrogen in bor• boranes 50 azines 118 Organic substituted aminoboranes 57 1,3,2-Diazaboracycloalkanes 134 Heats of formation of the series B-N Ring vibration of 1,3,2-diaza- BCI3_n[N(CH3)2]n 60 boracycloalkanes 135 Bisaminoboranes 69 1,3,2 -Benzodiheteroborolidines 139 Compounds with boron-metal bonds 70 2,1-Borazaronaphthalenes 144 Diborylamines 75 Boron-ll chemical shift data 157

721/9/65 - III/18/203