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Air Stable A*Bonded Ortho-Carborane Manganese Metal

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Air Stable A*Bonded Ortho-Carborane Manganese Metal 634 Bull. Korean Chem. Soc. 1995, Vol. 16, No. 7 Se-Jin Kim 이 al. 12. Hoshent J.; Kopelman, R. Phys. Rev. 1976, B14r 3438. 19. Strambini, G. B.; Galley, C. Chem. Phys. Lett. 1976, 39, 13. Allgren, D. C.; Monberg, E. M.; Kopelman, R. Chem. 257. Phys. Lett 1979, 64, 122. 20. Gobov, G. V.; Konashenko, V. I. Opt. Spectrosc. 1977, 43t 14. Stemlicht, H.; Nieman, G. C.; Robinson, G. W. J. Chem. 622. Phys. 1963, 38, 1326. 21. Gobov, G. V.; Surin, N. M. Vibronic Spectra of Aromatic 15. Hong, H-K; Kopelman, R. J. Chem. Phys. 1971, 55, 724. Compounds', Smolensk: Moscow, 1978; p 31. 16. Craig, D. P.; Walmsley, S. H. Excitons in Molecular Crys­ 22. Gobov, G. V.; Yudenkov, V. V.; Yurchenko, A. I. Present- tal^ Benjamin: New York, 1968. Day Aspects of Fine-Structure and Selective Spectroscopy; 17. Dexter, L. J. Chem. Phys. 1953, 21, 836. Sm이 eusk: Moscow, 1984; p 199. 18. Blumen, A.： Silbey, J. Chem. Phys. 1979, 70, 3707. Synthesis and Characterization of Air Stable a*Bonded ortho-carborane Manganese Metal Complexes 1 - [Mn(CO)5] -2-R-l ,2*cIoso-(a-C2Bi0Hio) and Their Conversion to the Stable ortho-carborane Substituted Fischer-type Carbene Complexes L[(CO)4Mn=C(OCH3)(C^3)]・2-R-l,2・ cfoso-CzBioHio (R=CH3, CeHs) Se-Jin Kim, Sijoon Lee\ Youhyuk Kim*, Jae-Jung Ko, and Sang Ook Kang* Department of Chemistry, College of Natural Sciences, Korea University, Chung-nam 339-700, Korea Yukong Limited, Taedok R&D Center, 140-1 Wonchon-dong, Yusung-Gu, Taejon, Korea ^Department of Chemistry, College of Natural Sciences, Dankook University,Chung-nam 330-714, Korea Received April 8, 1995 The metal-carbon o-bond cluster complexes l-Mn(CO)5-2-R-l,2-C2BioHi0 (R=CH3 la,(為氏 lb) have been prepared in good yields from readily available carboranyl lithium complexes, 1-Li+-2-R-l,2-C2BwHio- (R=CH3t C6H5)t by direct reaction with (CO)5MnBr. These manganese metal complexes are rapidly converted to the corresponding manganese metal carbene complexes, l-[(CO)4Mn=C(OCH3)(CH3)]-2-R-l,2-C2B]oH1o (R=CH3 Illa, C6H5 IIIb)t via alkylation with methyllithium followed by O-methylation with CF3SO3CH3. The crystal structure of Illb was determined by X-ray diffraction. Thus, complex Illb crystallizes in the orthorhombic space group P2)2i2i with cell parameters a—15.5537(5), b= 190697(5), c=7.4286(3) A, V=2203.4(1) A3, and Z=4. Of the reflections measured a total of 3805 unique reflections with F2>3o(F2) was used during subsequent structure refinement. Refinement converged to R)=0.053 and R2=0.091. Structural studies showed that the manganese atom had a slightly distorted pseudo-octahedral configuration about the metal center with the carbene and orfAo-carborane occupying the equatorial plane ds-orientation to each other. Introduction for the evidence they provide the ability of cluster to trans­ mit its influence to the metal. Recent study6 of carboranyl A series of extremely stable anionic chelated or^Ao-carbo- metal carbene system in which metal and carborane are sep­ rane-transition metal complexes containing unusually stable arated by one atom, have shown that some metal-carborane carbon-metal o-bonds has been reported.1'5 Previous study5 interaction occurs in such compounds. indicated that an extensive series of stable neutral manga- In this paper we wish to report on progress made towards nese(I) carborane complexes incorporating the l,2-C2Bi0Hn\ the syntheses of o-bonded ortho-carborane manganese metal l,10-C2B8H9_, and l,10-C2B8H82~ ligands 안 trough metal-car­ complexes and the formation of new manganese carbene bon o-bonds could be prepared. We now wish to report a complexes is discussed. Due to our interest in the structural compilation of results obtained on carborane l-R-l,2-C2BioHn features of manganese carbene complexes a single crystal containing manganese(I)-carbon a bonds and further conver­ X-ray diffraction determination of l-L(CO)4Mn=C(CXDH3)(CH3)] sion to a corresponding metal carbene species. -2-C6H5-lt2-C2BioH10 Illb was carried out. Thus, metal carbene complexes in which a carboranyl group is directly attached to the manganese metal in a o- Experimental Section bonded fashion adjacent to the metal carbene moiety are now to be studied. Cluster complexes of transition-metals Methods and Materials. The majority of solvents were of in which the metal atoms are directly bound are of interest reagent grade and were used without further purification. Synthesis of ortho-carborane Substituted Metal Carbene Complexes Bull. Korean Chem. Soc. 1995, Vol. 16, No. 7 635 Ethyl ether and THF were purified by distillation from lith­ stirred suspension of 1.65 g (6 mmol) of Mn(CO)sBr in 150 ium aluminum hydride, while 1,2-dimethoxyethane was fur­ mL of anhydrous ethyl ether. After stirring for 2 day at room ther purified by distillation from sodium-benzophenone. 1- temperature, the reaction mixture was rotary evaporated to Li+-2-CH3*l,2-C2BioHio , l-Li+-2-C5H6-l,2-C2BioHio_/'8 and give a brown oil. The oil was mixed with 50 mL of dry hexane Mn(CO)5Br9 were prepared by literature methods. All reac­ and the resulting mixture was placed atop a 1 in. X12 in. tions involving lithiocarboranes were carried out under ni­ column in hexane and was flash-chromatographed with 1: 9 trogen atmosphere. Silica gel was obtained from J.T. Baker ethyl ether-hexane mixture. The yellow band so eluted was Co. and was dried before use. rotary evaporated to near dryness and the residue was sub­ Physical Measurements. lH NMR spectra at 200 MHz limed at room temperature under high vacuum to give 1.58 and nB NMR spectra at 64.2 MHz were obtained on a Bru- g (4.5 mm아 , 75%) of bright yellow complex la. UB NMR ker AM-200 Fourier transform spectrometer. Selective pro- (64.2 MHz, ppm, CGD； 一 L0 (d, B9, Jbh = 140 Hz), -4.3 (d, ton-decoupled carbon-13 NMR spectra (50.3 MHz) were ob­ B12,/bh=130 Hz), — 6.3 (d, B&10, B45,/bh = 105 Hz), — 7.8 tained on the Bruker AM-200 spectrometer. All boron-11 (d, B711, B3,6,7bh=135 Hz);NMR (200.13 MHz, ppm, CM chemical shifts were referenced to BF3'O(C2H5)2 (0.0 ppm) 1.53 (s, CH3); exact mass calcd for uBi012C81Hi355Mni16O5 with a negative sign indicating an upfield shift. All proton 354.1069, found 354.1288; Anal. Calcd: C, 27.28; H, 3.72. and carbon chemical shifts were measured relative to inter­ Found: C, 28.05; H, 4.67. Rf=0.88 in Hexane; Mp=85-87 nal residual benzene from the lock solvent (99.5% CgDQ and t (dec); IR spectrum (KBr pallet, cm'1) 2990w, 2600s, 2570s, then referenced to Me4Si (0.00 ppm). High- and low-resolu­ 2550s, 2140s, 2050s, 2020s, 1455m, 1390w, 1200w, 1100m, tion mass spectra were obtained on a VG Micromass 7070H 1045m, 1030w, 945w, 810w, 750m, 660s, 640s, 615m sh, 550w, mass spectrometer. All melting points were uncorrected. Ele­ 430m. mental analyses were obtained from Schwazkopf Laborato­ l-[Mn(CO)5]*2*C6H5-lt2-c/oso*(G*C2BioHio) lb. A ries, Woodside, NY. solution of 6.45 mmol of 1-Li+-2-C6H5-1,2-C2BioHio_ in 80 Crystallographic Data for 1 -[(CO)4Mn=C(OCH3) mL of anhydrous ethyl ether was slowly added in a nitrogen (CH3)] -2-C6H5-1,2-C2B10H10 111b. Single crystals of Illb atmosphere to a rapidly stirred suspension of 1.76 g (6.4 were grown by slow evaporation inside a tube. A suitably mmol) of Mn(CO)5Br in 150 mL of anhydrous ethyl ether. sized crystal was placed inside a capillary tube, which was After stirring for 2 day at room temperature, the reaction then sealed with glue. This tube was mounted and trans­ mixture was evaporated to give a dark oil. The oil was dis­ ferred to the diffractometer. Refined cell dimensions and solved in 50 mL of benzene and the resulting solution was their standard deviations were obtained from least-squares rotary evaporated onto 2 g of predried silica gel. This mix­ refinement of 25 accurately centered reflections. ture was placed on a 1 in.X6 in. column in hexane, and a yellow band was eluted from the flash-chromatograph with X-ray Data Collection and Structure Solution and hexane. An additional 100 mL of eluent was collected. Rotary Refinement evaporation of the eluent to 50 mL gave white crystalline Diffraction data were collected on a Rigaku diffractometer needles of complex lb. A total of 1.50 g (3.62 mmol, 57%) with area detector employing graphite-monochromated Mo- was collected. Rotary evaporation to dryness gave 0.30 g of Ka radiation (A.=0.7107 A). X-ray data were processed, and a mixture of the product and Mn2(CO)i0. The white crystals the structure was solved and refined using the Molecular were sublimed and recrystallized from hexane. UB NMR (64. Structure Coporation teXan10 package on a Silicon Graphics 2 MHz, ppm, C6D6); 0.5 (d, B9, Jbh-130 Hz), -1.2 (d, B12, Indigo R4000 computer. A total of 16251 reflections was mea­ Jbh —160 Hz), ~4.2 (d, B&i。,/bh 드 100 Hz), — 5.3 (d, B45, 丿阳= sured over the range: 4<20<54°, — 19<h<19t —24<k<24, 140 Hz), -7.8 (d, B7,n, Jbh=145 Hz), —9.4 (d, B3,6, Jbh=140 -9<1<9.
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