Flash Vacuum Pyrolysis and computational studies on the [3,3]- and [3,5]-sigmatropic rearrangement of 6-acetoxy-2,4-cyclohexadienone derivatives have shown that the [3,5]-sigmatropic rearrangement is favored over the more familiar [3,3]-sigmatropic rearrangement. Electronic structure theory calculations suggested that the [3,5]-sigmatropic rearrangement proceeds via an allowed concerted pseudopericyclic transition state. The synthesis and thermal studies of other derivatives of cyclohexadienol such as trichloroacetimidates and xanthates will be discussed.

[3, 3]- and [3, 5]-Sigmatropic rearrangement of 6-hydroxy-2,4-cyclohexadienone derivatives

247th National Meeting (2014)

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