As part of a general program investigating novel aspects of [3,3]-sigmatropic rearrangements, we have recently begun examining azoles as platforms for these studies. Building on earlier work by the Kurth and Tunge groups, we have developed two approaches to N-allyl-S,N-ketene acetals. One approach involves a Horner-Wittig reaction using a phosphonate derived from benzothiazole, and the other approach begins with 2-alkyl(benzo)thiazoles. The ketene acetals undergo smooth rearrangement to 2-butenyl-thiazoles. Details of the studies and potential applications will be described.

[3,3]-Sigmatropic rearrangements of N-allyl-S,N-ketene acetals

243rd National Meeting (2012)

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