[3, 3]Sigmatropic Ring Expansion of Cyclic Thionocarbonates. VII. On the Formation of 8-Membered Thionocarbonates as the Intermediates

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In order to clarify the reaction mechanism of [3, 3]sigmatropic ring expansion of cyclic thionocarbonates, the 8-membered thionocarbonates (6 and 7) were synthesized by treatment of the corresponding diol monothionocarbonates (5 and 13) with lithium bis(trimethylsilyl)amide. However, reaction of 7 with meta-chloroperbenzoic acid afforded an 8-membered carbonate (14) in a quantitative yield.