Journal of the American Chemical Society

New synthetic reactions. A chemoselective approach to cleavage. alpha. to a carbonyl group via. beta.-keto sulfides. Preparation of 1, 2-diketones

BM Trost, GS Massiot

Index: Trost,B.M.; Massiot,G.S. Journal of the American Chemical Society, 1977 , vol. 99, # 13 p. 4405 - 4412

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Citation Number: 106

Abstract

Abstract:/3-Keto sulfides, available by the direct sulfenylation of enolates with diphenyl disulfide or phenyl benzenethiosulfonate, are acetoxylated by lead tetraacetate in warm benzene. The?-keto acetoxy sulfides represent a monoprotected form of a 1, 2-dicarbonyl compound. Oxidation and sulfoxide pyrolysis produce regiospecifically the monoenol acetate of the diketone. Treatment with iodine in methanol gives the monoketal. Exposure ...

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