New synthetic reactions. Sulfenylations and dehydrosulfenylations of esters and ketones

BM Trost, TN Salzmann, K Hiroi

Index: Trost,B.M. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 4887 - 4902

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Citation Number: 499

Abstract

Abstract: Quenching the enolates of esters and ketones with dimethyl disulfide or diphenyl disulfide produces the corresponding a-sulfenylated products. The regio-and chemospecificity of these reactions are defined. Oxidation to the sulfoxide followed by thermolysis leads smoothly to the@ unsaturated systems. Temperatures for the elimination of the phenyl sulfoxides are normally around 50 OC, whereas those for the methyl ...