Alkylation reactions with organometallic compounds. I. the reaction of methyltris(triphenylphosphine)rhodium with diphenylacetylene

M. Michman*, M. Balog

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

The reaction of diphenylacetylene with (Ph3P)3RhCH3 was studied in order to clarify the role of the organometallic compound as an alkylating reagent. Trans-α-methylstilbene was the main product of addition to the alkyne. The reaction is mostly an insertion process as concluded from studies with D2O. It was compared with the reaction of diphenylacetylene with the systems (Ph3P)3RhBr/CH3MgBr, and RhBr3·3H2O/CH3MgBr. With the first system mainly trans-α-methylstilbene was formed. In this reaction however, (Ph3P)3RhCH3 is shown not to be an active intermediate. With the second system, cis-addition was observed with a high degree of stereospecificity cis-α-methylstilbene being the main product. Condensation of diphenylacetylene to products like 1,2,3-triphenylnaphthalene, 1,2,3,4-tetraphenylbutadiene and 1,2,3,4-tetraphenylcyclopentadiene was also observed.

Original languageEnglish
Pages (from-to)395-402
Number of pages8
JournalJournal of Organometallic Chemistry
Volume31
Issue number3
DOIs
StatePublished - 16 Sep 1971

Fingerprint

Dive into the research topics of 'Alkylation reactions with organometallic compounds. I. the reaction of methyltris(triphenylphosphine)rhodium with diphenylacetylene'. Together they form a unique fingerprint.

Cite this