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Sigmatropic Rearrangement-Based Synthesis of 4-Alkenyl-1,3-dithiol-2-ones.

A series of conjugated 4-alkenyl-1,3-dithiol-2-ones have been prepared by microwave-assisted rearrangement of S-(4-acyloxy-2-alkynyl)- O-ethyl xanthates in moderate to good yields. The synthetic approach is based on a combination of [3,3] and [1,5] sigmatropic rearrangements as well as the intermediacy of a reactive betaine that induces the ionic elimination of the acyloxy group. The [1,5] sigmatropic rearrangement was confirmed by a deuterium-labeling experiment.