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Organic Seminar Abstracts UNIVERSITY OF IILINOIS LIBRARY AT U ^.NA-CHAMPAIGN Digitized by the Internet Archive in 2012 with funding from University of Illinois Urbana-Champaign http://archive.org/details/organicsemi1979821univ 1 SEMINAR TOPICS X- I Semester 1979-80 — ^ Generation and Synthetic Utility of Carbanions Stabilized by Divalent Sulfur Peter Becker The Design, Synthesis, and Biology of Intercalating Agents David W. Robertson r HERTZBERG - NEW METHOD, INC. EAST VANDALIA ROAD, JACKSONVILLE, ILL. 62650 J - Q_ , TITUE NO. ACCOUNT NO. LOT AND TICKET NO. ...13 B ]• 22 : NRTK« 31 5>79~82*PT Q* 547*IG»L< 33 CLOTH COLOR CHARGING INFORMATION .... 36 STUBBING FRONT COVER HAND SEW NO TR IM THRU SEW PAGES LAMINATED THRU SEW ON TAPE EXTRA THICKNESS ... .46 HAND ADHESIVE MAP POCKET PAPER LENGTHWISE MAP POCKET CLOTH SPECIAL WORK AND PREP. FOREIGN TITLE SPECIAL WORK LINES OF LETTERING 56 Phosphorus uompouiiub Stephen D. Harper Vanadium- and Molybdenum-Catalyzed of Olefins with Epoxidations 59 Alkyl Hydroperoxides - John R. Hurst Characterization of Certain Detection and 68 Carbon Diradicals Via ESR and CIDNP... G. H. Slocum 76 Enzymic Catalysis in Organic Synthesis Venkatesalu Bakthavachalam in the Reactions of Regioselectivity 86 Hetero-Substituted Allylic Carbanions, Dale Kempf SEMINAR TOPICS I Semester 1979-80 - T* Generation and Synthetic Utility of Carbanions Stabilized by Divalent Sulfur 1 Peter Becker The Design, Synthesis, and Biology of Intercalating Agents 3 David W. Robertson Modification of Olefins with Organo- Selenium Reagents 13 Larry D. Boardman Synthetic Methods for the Preparation of Sterically Hindered Olefins 22 Ronald S. Michalak Mechanistic Considerations in 1,3-Dipolar Cycloadditions 31 Clark Cummins Applications of Lasers in Organic Chemistry 33 Rick Gdanski Magnetic Field Effects on Chemical Reactions in Solution 36 Paul Gelburd Synthetic Approaches to Biotin 46 Jack Muskopf Stable Hexacoordinate Organo- Phosphorus Compounds 56 Stephen D. Harper Vanadium- and Molybdenum-Catalyzed Epoxidations of Olefins with Alkyl Hydroperoxides 59 John R. Hurst Detection and Characterization of Certain Carbon Diradicals Via ESR and CIDNP 68 G. H. Slocum Enzymic Catalysis in Organic Synthesis 76 Venkatesalu Bakthavachalam Regioselectivity in the Reactions of Hetero-Substituted Allylic Carbanions 86 Dale Kempf Modern Methods for the De oxygenation of Alcohols 96 William Stevenson •Enantiomerically Unusual Bioraolecules 104 Anthony W. Czarnik Transition State Analogs as Enzyme Inhibitors 108 David Kinder -1- GENERATION AND SYNTHETIC UTILITY OF CARBANIONS STABILIZED BY DIVALENT SULFUR Reported by Peter Becker September 6, 1979 Organometallic compounds stabilized by an adjacent sulfur atom are well known and synthetically useful. This survey is limited to carbanions stabilized by a single divalent sulfur atom. Thioanisole was first metallated on the methyl group by Gilman and Webb 1 by reaction with n-butyllithium at elevated temperatures; however, cleavage and ring metallation were serious side reactions. Corey found that addition of 1,4-diazabicyclooctane increased the yield of l. 2 Peterson formed 2 from dimethylsulfide using n-butyllithium/tetramethyl- ethylenediamine. Recently Dolak and Bryson deprotonated isobutylphenyl sulfide with _ter_t-butyllithium in tetrahydrofuran/hexamethylphosphoric 1 5 6 7 8 triamide. * Exchange with boron, sulfur, selenium, and tin also gives a-lithio sulfides. ex .*»».> Y <^ I R—S—CH 2 Li R—S— 5^-R' . C=SCH 2 Li TLl y + 1 R = Ph Y -3 2 R = Me A Reaction of a-lithiosulfides with a variety of electrophiles gives the expected products in good yield; j2.j>. 2^ with carbon dioxide gives 2-methylthioacetic acid. Methylenation of ketones 10 has been performed with 1> and 1_ along with higher homologs has been used in the synthesis of 11 12 epoxides. Homologation of trialkyl boranes has been effected with 2^, as well as the synthesis of terminal alkynes from carboxylic acids. 13 Trost has formed cyclobutanones 14 and cyclopentenes 15 from adducts of phenylthiocyclopropyl lithium with ketones. Allyl and benzyl sulfides are more readily metallated, and even the dianions of allyl and benzyl thiol 16 have been reported. Trialkyl borane complexes 17 and complexation with heteroatoms 18 have been used to direct a-alkylation of ambident allyl anion J3. However, the copper reagent gives 21 predominantly y- alkyla t ion. 19 Reported syntheses of terpenes, 20 jasmonoids and F 22 prostaglandin 2 employed species J3. Cecropia juvenile hormones have been made via dihydrothiapyrans. 23 Alkylation followed by sigmatropic rearrangement has proven useful. 24 Metallated vinyl sulfides serve as acyl anion equivalents and have been prepared by addition of organometallic reagents to acetylenic sulfides 25 proton is the and thioketenes and transmetallation. Direct abstraction or most widely used route and there have been a number of recent examples. D Metallation of 1,3-dien-l-yl sulfides has also been reported. 27 Higher homologs have been metallated in the a-position. 28 Derivatives of thiols such as thioimidates, dithiocarbonates and thio- esters have been deprotonated on the sulfur-bearing carbon and are thought 29 to be dipole stabilized 4_. Mono and dithiocarbamates also have been deprotonated. 30 The above compounds are generally limited to the methyl and allyl cases; however, a-lithioisopropyl 2,4,6-triisopropylthio- benzoate has been formed in good yield. 31 -2- BIBLIOGRAPHY 1. H. Gillman and F. J. Webb, J. Am. Chem. Soc, 71, 4062 (1949). 2. E. J. Corey and D. Seebach, J. Org. Chen., 31, 4097 (1966) 3. D. J. Peterson, ibid ., 32, 1717 (1967). 4. T. M. Dolak and T. A. Bryson, Tetrahedron Lett., 1961 (1977). 5. A. Mendoza and D. S. Matteson, J. Org. Chem., 44, 1352 (1979). 6. C. G. Screttas and M. Micha-Screttas, ibid. , 44, 713 (1979); T. Cohen, W. M. Daniewski and R. B. Weisenfeld, Tetrahedron Lett., 4665 (1978). 7. A. Anciaux, A. Eman, W. Damonc, and A. Krief, ibid . , 1617 (1975); D. Seebach, N. Meyer, and A. K. Beck, Ann. Chem., 846 (1977). 8. D. J. Peterson, Organomet. Chem. Rev., A 2, 295 (1972). 9. C. Pichat and J. P. Beaucourt, J. Label. Com., 10, 103 (1974). 10. I. Kawajima, S. Sato, and Y. Kurata, Tetrahedron Lett., 737 (1972); T. Shono, et al. , ibid . , 2807 (1978); R. L. Sowerby and R. M. Coates, J. Am. Chem. Soc, 94, 4758 (1972). 11. J. R. Shanklin, e_t al . , J. Am. Chem. Soc, 95_, 3429 (1973); W. H. Pirkle and P. L. Rinaldi, J. Org. Chem., 43, 3803 (1978); W. H. Pirkle and P. L. Rinaldi, ibid., 44, 1025 (1979). 12. E. Nigishi, et al., J. Org. Chem., 40, 814 (1975). ___. 13. S. Kano, T. Yokomatsu, and S. Shibuya, ibid . , 43 , 4366 (1978). 14. B. M. Trost, et al. , J. Am. Chem. Soc, 99, 3080,3088 (1977); B. M. Trost and J. H. Rigby, J. Org. Chem., 43, 2938 (1978); B. M. Trost and W. C. Vladchick, Synthesis, 821 (1978). 15. B. M. Trost and D. E. Keeley, J. Am. Chem. Soc, 98, 248 (1976). 16. D. Seebach and K.-H. Geiss, Angew. Chem., 86^, 202 (1974); M. Pohmakotr, K.-H. Geiss, and D. Seebach, Chem. Ber., 112, 1420 (1979). 17. Y. Yamamoto, H. Yatagai, and K. Maruyama, J. Chem. Soc, Chem. Commun., 157 (1979). 18. H. Narasaka, M. Hayashi, and T. Mukaiyama, Chem. Lett., 259 (1972). 19. K. Oshima, et al., Bull. Chem. Soc. J., 48, 1567 (1975). 20. R. M. Coates, D. A. Ley, and P. L. Cavender, J. Org. Chem., 43, 4915 (1978); M. Kodama, Y. Matsuki, and S. Ito, Tetrahedron Lett., 1121 (1976); J. F. Biellmann and J. B. Ducep, ibid., 3707 (1969); E. E Van Tamelen, et al., J. Am. Chem. Soc, 94, 8228 (1972). 21. J. F. Biellmann and D. Schirlin, Syn. Coram. , 8, 409 (1978). 22. E. J. Corey and R. Noyori, Tetrahedron Lett., 311 (1970). 23. P. L. Sotter and R. E. Hornish, J. Am. Chem. Soc, 95_, 4444 (1973). 24. Thiaclaisen, L. Brandsma, and H. D. Verkraijsse, Rec Trav. Chim. Pays-Bas, 9^, 319 (1974); K. Oshima, H. Yamamoto, and H. Nozaki, J. Am. Chem. Soc, 95, 4446 (1973). Oxycope: D. A. Evans, ibid ., 100 , 2242 (1978). 25. B.-T. GrSbel and D. Seebach, Synthesis, 357 (1977) and references cited in section 5.1. 26. R. C. Cookson and P. J. Parsons, J. Chem. Soc, Chem. Commun., 990 (1976) and 821,822 (1978). 27. R. H. Everhardus, H. G. Eeuwhorst, and L. Brandsma, J. Chem. Soc, Chem. Commun., 801 (1977); R. Grafing and L. Brandsma, Synthesis, 578 (1978); R. H. Everhardus, R. Grafing and L. Brandsma, Rec Trav. Chim. Pays-Bas, 97, 69 (1978). 28. R. Muthukrishman and M. Schlosser, Helv. Chim. Acta, _59, 13 (1976); J. J. Fitt and H. W. Gshwend, J. Org. Chem., 44, 303 (1979). 29. P. Beak and D. B. Reitz, Chem. Rev., _78, 275 (1978) and references cited in section IV. 30. T. Hayashi, A. Sakurai, and T. Oishi, Chem. Lett., 1483 (1977); T. Nakai, T. Mimura, and A. Ari-Izumi, Tetrahedron Lett., 2425 (1977) and references cited therein. 31. P. Beak and P. Becker, unpublished results. ^ -3- THE DESIGN, SYNTHESIS, AND BIOLOGY OF DNA INTERCALATING AGENTS Reported by David W. Robertson September 27, 1979 Intercalation is the noncovalent insertion of planar aromatic mole- cules between two successive base pairs of double-helical DNA. Since Lerman's classic delineation of intercalation 1 over two decades ago, many antitumor agents, mutagens, carcinogens, and teratogens have been found to exert their effects through intercalative binding to DNA. Because of the biological and clinical importance of intercalation, molecular biologists, oncologists, and chemists have intensively investigated the nature of this phenomenon. In this paper the evidence adduced for intercalation will be surveyed, and the design, synthesis, and biological applications of DNA intercalating agents will be examined. Structural Requirements for Intercalation . Ethidium bromide (1) , a phenanthridinium trypanocide, and proflavin (2), a powerful frameshift mutagen, 2 are archetypical intercalators (Figure 1) . Both inhibit DNA and RNA synthesis and are two of the more widely studied intercalators.
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