Oxidative seco rearrangement. A novel carbon-carbon bond cleavage

BM Trost, K Hiroi, LN Jungheim

Index: Trost, Barry M.; Hiroi, Kunio; Jungheim, Louis N. Journal of Organic Chemistry, 1980 , vol. 45, # 10 p. 1839 - 1847

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Citation Number: 24

Abstract

Trost, Hiroi, and Jungheim compounds with lead tetraacetate under many different conditions led to no detectable ring cleavage. We were able to isolate 2-acetoxy-2- (methylthio)-(or (phenylthio)) cyclohexanone. Reasoning that the initial attack occurred at sulfur to give 2 but that CC bond cleavage was too slow relative to sulfur serving as a leaving group to give 3 and 4, we felt we might achieve ring cleavage if the ionization of ...

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