Tetrahedron

Thermally initiated reactions of (z)-epoxyhexenynes a facile preparation of 3, 4-annulated furans

W Eberbach, J Roser

Index: Eberbach, Wolfgang; Roser, Joachim Tetrahedron, 1986 , vol. 42, # 8 p. 2221 - 2234

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Citation Number: 23

Abstract

An efficient and general access to 3, 4-annulated 2-vinylfurans (type II) is provided by the thermally induced ring transformation of epoxyhexenynes (I). Depending on the substitution pattern the reactions proceed either by heating in solution (5a-h) or under short-time thermolysis conditions (61, j). The results are consistent with a multistep mechanism involving 1-oxacyclohepta-3, 4, 6-trienes as central intermediates.