Keten dithioacetals. Part 22. Reaction of polarised ketoketen dithioacetals with dimethyl acetylenedicarboxylate

Vishwakarma, Jai N. ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1983) Keten dithioacetals. Part 22. Reaction of polarised ketoketen dithioacetals with dimethyl acetylenedicarboxylate Journal of the Chemical Society, Perkin Transactions 1 . pp. 1099-1102. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1983...

Related URL: http://dx.doi.org/10.1039/P19830001099

Abstract

Ketoketen dithioacetals (1a-e) react with dimethyl acetylenedicarboxylate (2) to give open-chain dienes (4a-e) respectively. The formation of these dienes is explained through ring opening of the cyclobutene formed by [2 + 2]cycloadditions of (1) and (2). The cyclic ketoketen dithioacetal (9) reacted with (2) to give an unusual compound, which was characterized as thiapyran-2-one (10). A plausible mechanism for the formation of (10) has been suggested.

Item Type:Article
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