Helvetica chimica acta

2??Vinylcyclobutanones by Cycloaddition of Vinylketenes to Simple Olefins

DA Jackson, M Rey, AS Dreiding

Index: Jackson, David A.; Rey, Max; Dreiding, Andre S. Helvetica Chimica Acta, 1983 , vol. 66, # 7 p. 2330 - 2341

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Citation Number: 21

Abstract

Abstract Selected [2+ 2]-cycloadditions of three alkylvinylketenes 2 to one mono-and seven dialkyl-olefins 3 yielded eleven 2-alkyl-2-vinylcyclobutanones 4 (Tables 1 and 2). Three methods were compared, all involving in situ generation of the ketenes 2 by HCl-elimination from α, β-unsaturated acid chlorides 1; the most effective employed a large excess of olefin 3 and a high reaction temperature. The [2+ 2]-cycloadditions were fully regio-and ...