O-lithiothiophenol equivalents: Generation, reactions, and applications in synthesis of hindered thiolate ligands

Journal of the American Chemical Society

Volumn 111, Issue 2, 1989, Pages 658-665

  Block, Eric ^a   Eswarakrishnan, Venkatachalam ^a   Gernon, Michael ^a   Ofori Okai, Gabriel ^a   Saha, Chantu ^a   Tang, Kaluo ^a   Zubieta, Jon ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845184962     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00184a039     Document Type: Article

References (15)

1. (a) Presented in part at the Ninth International Symposium on Sulfur Chemistry, Nijmegen, The Netherlands, June, 1986, the First International Conference on Heteroatom Chemistry, Kobe, Japan, July 1987, and the Eleventh International Symposium on Heterocyclic Chemistry, Heidelberg, West Germany, August 1987. (b) For brief mention of this work and a general review of the chemistry of mixed organosilicon-sulfur compounds, see: Block, E.; Aslam, M. Tetrahedron 1988, 44, 281. Block, E. Rev. Heteroatom Chem. 1988, 1, 163.
2. (a) Dance, I. G. Polyhedron 1986, 5, 1037. (b) Blower, P. G.; Dilworth, J. R. Coord. Chem. Rev. 1987, 76, 121.
3. Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161. Gutsche, C. D. Top. Curr. Chem. 1986, 51, 742, and references therein.
4. For example, see: Olmstead, M. M.; Sigel, G.; Hope, H.; Xu, X.; Power, P. P. J. Am. Chem. Soc. 1985, 107, 8087.
5. (a) Bailey, F. P.; Taylor, R. J. Chem. Soc. B 1971, 1446. (b) Ortholithiation of aryl sulfones and arenesulfonates and dilithiation of aryl alkyl sulfides is known: Figuly, G. D.; Martin, J. C. J. Org. Chem. 1980, 45, 3728. Stoyanovich, F. M. Izv. Akad. Nauk. SSSR, Ser. Khim. 1980, 1, 145. Krizan, T. D.; Martin, J. C. J. Am. Chem. Soc. 1983, 105, 6155. Bonfiglio, J. N. J. Org. Chem. 1986, 51, 2833. Cabiddu, S.; Florida, C.; Malis, S. Tetrahedron Lett. 1986, 27, 4625.
6. (a) Block, E.; Aslam, M. J. Am. Chem. Soc. 1985, 107, 6729. (b) Parham, W. E.; DeLaitsch, D. M. J. Am. Chem. Soc. 1954, 76, 4962. (c) Seebach, D.; Meyer, N.; Beck, A. K. Justus Liebigs Ann. Chem. 1977, 846. (d) Kruse, C. G.; Broekhof, N. L. J. M.; Van der Gen, A. Tetrahedron Lett. 1976, 1725. (e) Grillot, G. F.; Felton, H. R.; Garrett, B. R.; Greenberg, H.; Green, R.; Clementi, R.; Moskowitz, M. J. Am. Chem. Soc. 1954, 76, 3869.
7. Posner, G. H.; Canella, K. A. J. Am. Chem. Soc. 1985, 107, 2571.
8. (a) Figuly, G. D. Ph.D. Thesis, University of Illinois—Urbana, 1981. (b) Figuly, G. D.; Loop, C. K.; Martin, J. C. J. Am. Chem. Soc., preceding paper in this issue. (c) For earlier efforts to prepare lithium 4-lithiobenzenethiolate from 4-bromothiophenol, see: Gilman, H.; Gainer, G. C. J. Am. Chem. Soc. 1947, 69, 1946. Jones, R. G.; Gilman, H. Org. React. 1951, 6, 339.
9. For a recent related example, see: Macdonald, J. E.; Poindexter, G. S. Tetrahedron Lett. 1987, 28, 1851.
10. Maiolo, F.; Testaferri, L.; Tiecco, M.; Tingoli, M. J. Org. Chem. 1981, 46, 3070. Hunig, S.; Fleckenstein, E. Justus Liebigs Ann. Chem. 1970, 738, 192. Degani, I.; Fochi, R. J. Chem. Soc., Chem. Commun. 1976, 471. Dirk, C. W.; Cox, S. D.; Wellman, D. E.; Wudl, F. J. Org. Chem. 1985, 50, 2395.
11. (a) Block, E.; Gernon, M.; Kang, H.; Zubieta, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1342. (b) Block, E.; Gernon, M.; Kang, H.; Liu, S.; Zubieta, J. J. Chem. Soc., Chem. Commun. 1988, 1031. Block, E.; Kang, H.; Ofori-Okai, G.; Zubieta, J. Inorg. Chim. Acta 1989, 156, 27. Block, E.; Gernon, M.; Kang, H.; Ofori-Okai, G.; Zubieta, J. Inorg. Chem., in press.
12. Miyashita, N.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
13. Newman, M. S.; Karnes, H. A. J. Org. Chem. 1966, 31, 3980.
14. Gilman, H.; Beaber, N. J. J. Am. Chem. Soc. 1925, 47, 1449.
15. Lumbroso, L.; Liégeois, CH.; Testaferri, L.; Tiecco, M. J. Mol. Struct. 1986, 144, 121.