Studies of Benzoylsulfene. IV. The Cycloaddition Reactions of Benzoylsulfene with Cinnamylideneamines

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書誌事項

公開日
1971
DOI
  • 10.1246/bcsj.44.2750
公開者
公益社団法人 日本化学会

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説明

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.

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