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doi:10.1016/S0040-4039(00)83980-5 
Copyright © 1986 Published by Elsevier Science Ltd. All rights reserved.
Yoshihiko Watanabe, *, Yoshio Ueno, Takumi Araki, Takeshi Endo and Makoto Okawara
Research Labolatory of Resources Utilization, Tokyo institute of Technology, Nagatsuta, Midoriku, Yokohama 227 Japan
Received 14 November 1985.
Abstract
(Alkylsulfonyl) benzothiazole 1 reacted with tributyltin hydride in the presence of azobisisobutyronitrile at 80°C to give 2-(tributylstannyl) benzothiazole in 67–79% yield. Similarly, vinylsulfone
gave the corresponding vinylstannane in 58–78% yield.
References
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J. Dupuis, B. Giese, J. Hartung and M. Leising J. Am. Chem. Soc. 107 (1985), p. 4332. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (19)
In all cases, a small amount of benzothiazole was isolated in 5–10% yield. All new compounds showed satisfactory physical and spectral data.
The eliminated sulfonyl radical (·SO2CH2COCH3) may cleave to sulfur dioxide and acetonyl radical prior to the formation of stannylsulfinate (Bu3SnOSOCH2COCH3). Acetonyl radical may give eventually acetone.
The stereochemistry of
was estimated by 1H NMR. The trans isomer (98%) was formed predominantly A.J. Leusick, H.A. Budding and J.W. Marsman J. Organometal. Chem. 9 (1967), p. 285.
D. Milstein and J.K. Stille J. Am. Chem. Soc. 101 (1979), p. 4981. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (46)
D. Milstein and J.K. Stille J. Am. Chem. Soc. 101 (1979), p. 4992. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (128)
E.J. Corey and R.H. Wollenberg J. Am. Chem. Soc. 96 (1974), p. 5581. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (46)
W.P. Neumann and E. Heymann Ann. Chem. 683 (1965), p. 24. Full Text via CrossRef
M. Fiorentino, L. Testaferri, M. Tiecco and L. Troisi J. Chem. Soc. 316 (1977) Chem. Comm. .
M.Julia etal. reported the tributyltin hydride catalyzed cis-trans isomerization of vinylsulfone, although they can not obtain substituted products described here. M. Julia, C. Rolando and J.N. Verpeaux Tetrahedron Lett. 23 (1982), p. 4319 Their postulation (addition and elimination of tin radical, eq 1) seems to be unlikely, since we have already confirmed the exclusive splitting of sulfonyl radical but not tin one in a closely related system (eq 2). . Abstract | 
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Y. Ueno, S. Aoki and M. Okawara J. Am. Chem. Soc. 101 (1979), p. 5414 Julia's result can be explainedby the partial electron transfer leading to the intermediate similar to the anion-radical tin-cation complex. . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (17)
