Thermal rearrangement of alkynyl three-membered rings. Evidence for an oxacycloheptatriene intermediate

F Bourelle-Wargnier, M Vincent…

Index: Bourelle-Wargnier, Francoise; Vincent, Marcel; Chuche, Josselin Journal of Organic Chemistry, 1980 , vol. 45, # 3 p. 428 - 435

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Citation Number: 17

Abstract

The substituted ethynylvinyloxiranes 9a-e were obtained by condensation of vinylsulfonium ylides with acetylenic carbonyl compounds. Thermolysis of the cis isomers of 9 was investigated in both the gas phase and the liquid phase. The first procedure afforded only cyclopropanecarboxaldehydes 17a-e, the stereochemistry of which depended on the nature and position of the substituents and on the experimental conditions. In the liquid phase 9a ...