Journal of Organic Chemistry p. 2224 - 2228 (1985)
Update date:2022-08-02
Topics:
Abou-Gharbia, Magid
Ketcha, Daniel M.
Zacharias, David E.
Swern, Daniel
The reactions of diphenylketene and tert-butylcyanoketene with several sulfilimines were investigated. 5,5-Diphenyl-2-oxazolin-4-ones were produced from N-acylsulfilimines and diphenylketene while a 2-indolinone was obtained from N-arylsulfilimine and the same ketene. tert-Butylcyanoketene afforded either simple substituted or ortho-rearranged amides when S,S-dimethylsulfilimines were used as substrates.The structure of 2,5,5-triphenyloxazolidin-4-one (7b) was confirmed by single-crystal X-ray examination.Possible mechanistic pathways which account for all observed products are discussed.
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Doi:10.1246/bcsj.58.1723
(1985)Doi:10.1055/s-1984-31022
(1984)Doi:10.1021/ja00302a011
(1985)Doi:10.1021/ja01119a042
(1953)Doi:10.1021/jo00217a030
(1985)Doi:10.1016/S0040-4039(00)79085-X
(1992)
