Tetrahedron

Additive Pummerer reactions of vinylic sulfoxides. Synthesis of γ-hydroxy-α, β-unsaturated esters, α-hydroxyketones, and 2-phenylsulfenyl aldehydes and primary …

D Craig, K Daniels, AR MacKenzie

Index: Craig, Donald; Daniels, Kevin; MacKenzie, A. Roderick Tetrahedron, 1993 , vol. 49, # 48 p. 11263 - 11304

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Citation Number: 53

Abstract

Treatment of β-monosubstituted vinylic sulfoxides 1 with trifluoroacetic anhydride in dichloromethane gave excellent yields of 1, 2-bis (trifluoroacetoxy) thioethers 6. Mildly basic methanolysis of 2-alkyl-substituted 6 gave α-hydroxyaldehydes 11 as monomer-dimer mixtures; similar treatment of the 2-aryl analogues afforded aryl (hydroxymethyl) ketones 12. Compounds 11 underwent Wittig reactions with ...

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