Unusual triethylamine catalyzed rearrangement of bicyclic endoperoxides derived from substituted cycloheptatrienes

Article abstract of DOI:10.1016/S0040-4020(97)00630-3

Triethylamine catalyzed rearrangement of the substituted bicyclic cycloheptatriene endoperoxides 9, 10, 12, 13, 20, 21, 22 and 30 underwent different reaction modes and resulted in the formation of ring contraction products in the case of 9, 10, 12 and 13. However, 20, 21, and 30 provided rearranged diketones 23, 24 and 32 almost in quantitative yield. The mechanism of these reactions was discussed.