Alkylation reactions with organometallic reagents. III. The effect of oxygen on alkylation reactions with cobalt(I) compounds

M. Michman*, B. Steinberger, S. Gershoni

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

Methylmagnesium bromide reacts with diphenylacetylene in the presence of cobalt(I) and cobalt(II) complexes. Oxygen is shown to have a significant effect on the reaction. Under argon the alkyne is consumed either by formation of cyclisation products or by addition across the triple bond to yield stilbene derivatives and 1,2-diphenylpropene (by mono-alkylation of the triple bond). Under oxygen the consumption of the alkyne through condensation tends to be blocked while the yield of addition reactions to the triple bond increases and includes the formation of 2,3-diphenylbut-2-ene (by dialkylation of the alkyne). The same effect to a smaller extent is observed when CH3Co(Ph3P)3 reacts with PhCCPh. An attempt to rationalize the oxygen effect is presented.

Original languageEnglish
Pages (from-to)293-302
Number of pages10
JournalJournal of Organometallic Chemistry
Volume113
Issue number3
DOIs
StatePublished - 29 Jun 1976

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