1-Phenyl-2,2-divinylcyclopropanes are discovered to undergo sigmatropic rearrangements by substrate-dependant pathways. Some substrates react by a known vinylcyclopropane rearrangement pathway, while others can be diverted to a novel sigmatropic pathway. We present a variety of substrates and conditions to explore the scope and limitations of these rearrangements. We also present some insights about the reaction mechanism.

Sigmatropic rearrangements of some divinylcyclopropanes

245th National Meeting (2013)

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