Rhodium(I)-catalyzed intramolecular ene reaction of vinylidenecyclopropanes and alkenes for the formation of bicyclo[5.1.0]octylenes

Wei Li, Wei Yuan, Min Shi, Erik Hernandez, Guigen Li

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

"Chemical Equation Presented" An efficient catalytic system for the intramolecular ene reaction of allene and alkene of diarylvinylidenecyclopropanes has been established. The reaction was achieved by using [RhCl(CO)2]2 as the catalyst in co-solvents of toluene and acetonitrile. MeCN was found to play a crucial role in controlling the reaction toward formation of bicyclo[5.1.0]octylene derivatives. An alternative system consisting of [RhCl(CO)2]2 and toluene in the absence of MeCN was found to give [2 + 2] cycloaddition adducts. The structures have been unambiguously determined by X-ray structural analysis. Deuterium labeling experiments were conducted to confirm the mechanism hypothesis.

Original languageEnglish
Pages (from-to)64-67
Number of pages4
JournalOrganic Letters
Volume12
Issue number1
DOIs
StatePublished - Jan 1 2010

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