Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies of Benzoylsulfene. IV. The Cycloaddition Reactions of Benzoylsulfene with Cinnamylideneamines
Otohiko TsugeSumio Iwanami
Author information
JOURNALS FREE ACCESS

1971 Volume 44 Issue 10 Pages 2750-2755

Details
Abstract

The reaction of benzoylmethanesulfonyl chloride with cinnamylideneamines in the presence of triethylamine has been investigated; the products were identified, by spectral studies as well as by chemical transformations, as the corresponding Diels-Alder adducts of benzoylsulfene as a dienophile to the α,β-unsaturated anils, 2-substituted 5H, 6H-6-benzoyl-5-phenyl-1,2-thiazine 1,1-dioxides, in which the phenyl and benzoyl groups are quasi-equatorial and quasi-axial respectively. The cycloadducts underwent inversion, on treatment with sodium methoxide in methanol or with silica gel in chloroform, to the corresponding epimers, in which both the phenyl and benzoyl groups are quasi-equatorial.

Information related to the author

This article cannot obtain the latest cited-by information.

© The Chemical Society of Japan
Previous article Next article
feedback
Top