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Insertion of unactivated acetylenes into the metal-aryl bond of bis(triphenylphosphine)phenylbromonickel(II)

Authors
Journal
Journal of Organometallic Chemistry
0022-328X
Publisher
Elsevier
Publication Date
Volume
140
Issue
1
Identifiers
DOI: 10.1016/s0022-328x(00)84405-8

Abstract

Abstract 2-Butyne reacts stereospecifically with (PPh 3) 2Ni(Ph)(Br) in CH 3OH at room temperature, leading to the isolable vinyl complex trans-(PPh 3) 2-Ni(Br)[ cis-C(CH 3)C(CH 3)(Ph)] in 70% yield. Carbonylation (CO/CH 3OH) of this material gives a 98% yield of cis-α,β-dimethylcinnamate. Reaction of the phenylnickel complex with 3-hexyne is more complicated; insertion again occurs, but the ultimate products of the reaction are phenyl-substituted styrenes and butadienes. Evidence is presented that free vinyl radicals are involved as intermediates in the 3-hexyne reaction.

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