On a mechanism for the trans-addition of alkylmagnesium and alkylrhodium derivatives to diphenylacetylene

Michael Michman*, Sophia Weksler-Nussbaum

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The reaction of diphenylacetylene with tris(triphenylphosphine)rhodium bromide yields 1,2-diphenylpropene mostly as the trans-isomer. When reactions are terminated with D2O it is shown that trans-1,2-diphenylpropene is deuteriated at the vinylic position and at the ortho-position of the aromatic ring adjacent to the methyl group. The cis-isomer is deuteriated at the vinylic position only. These results offer an explanation of the mechanism of trans-addition in this case. Possible implications for other cases of trans-addition are discussed.

Original languageEnglish
Pages (from-to)872-875
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number9
DOIs
StatePublished - 1978

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