Studies on structurally simple αβ-butenolides. IV. behaviour of protoanemonin as electrophile towards alcohols and thiols

A. Calderon, J. Font, R. M. Ortuno

Research output: Contribution to journalArticleResearchpeer-review

12 Citations (Scopus)

Abstract

Protoanemonin, reacts in different ways with thiolate and alkoxide anions. Thus, while the very soft nucleophile benzenethiolate attacks exclusively the olefinic carbons of 1, alkoxides always attack the carbonyl group in the first step of the reaction. In intermediate cases, when neither very hard nor very soft nucleophiles are used, regioselectivity is not observed. Mechanisms are discussed to explain this differential reactivity. © 1984.
Original languageEnglish
Pages (from-to)3787-3794
JournalTetrahedron
Volume40
Issue number19
DOIs
Publication statusPublished - 1 Jan 1984

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