Helvetica Chimica Acta

Die Cope??Umlagerung als Prinzip einer repetierbaren Ringerweiterung

J Bruhn, H Heimgartner, H Schmid

Index: Bruhn,J. et al. Helvetica Chimica Acta, 1979 , vol. 62, p. 2630 - 2654

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Citation Number: 18

Abstract

Summary Starting with the unsaturated 8-ketoesters of type I, a vinyl group is introduced into the P-position by 1, 4-addition of vinyl magnesium chloride to give I1 (Scheme 3). Treatment of the P-ketoester TI with phenyl vinyl sulfoxide in the presence of sodium hydride yields the sulfoxides 111, which on thermolysis lead to the a, P-divinyl ketoesters of type IV via elimination of sulfinic acid (Scheme 3). The Cope-System IV undergoes rearrangement to ...