Synthesis of thiophenes from allenyl sulfones involving α, β??unsaturated sulfines as intermediates

JB van der Linden, PFTM van Asten…

Index: Linden, Johannes B. van der; Asten, Peter F. T. M. van; Braverman, Samuel; Zwanenburg, Binne Recueil des Travaux Chimiques des Pays-Bas, 1995 , vol. 114, # 2 p. 51 - 60

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Citation Number: 14

Abstract

Abstract The synthesis of thiophenes starting from allenyl sulfones, via intermediate formation of α, β-unsaturated sulfines, is described. The allenyl sulfones were synthesized by a [2, 3]-sigmatropic rearrangement of appropriately substituted prop-2-ynyl sulfinates. Treatment of the allenyl sulfones with n-butyllithium and chlorotrimethylsilane gave α- silylated allenyl sulfones in almost quantitative yield, which, on heteroconjugate addition ...