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Metal Catalysis in Organic Reactions. Part 13. The Reaction of 3-En-1-ynes with Trialkylalanes: Influence of Transition-metal Complexes

DOI: 10.1039/P19810001900

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1900 - 1908 (1981)

Update date:2022-08-05

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Authors:

Caporusso, Anna MariaCaporusso, Anna Maria

Giacomelly, GiampaoloGiacomelly, Giampaolo

Lardicci, LucianoLardicci, Luciano

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Article abstract of DOI:10.1039/P19810001900

The reaction between trialkylalanes and 3-alkyl-, or 4-alkyl-, or 3,4-dialkyl-but-3-en-1-ynes (1) lead to products which correspond to metallation, reduction, and carbalumination processes.The extent of such reactions, and the regio- and stereo-selectivity of the carbalumination, are dependent on the enyne used.A mechanism is proposed involving tautomeric equilibria among several α-unsaturated organoaluminium intermediates to explain the formation of the carbalumination products. In the presence of catalytic amounts of nickel and manganese complexes, 3-en-1-ynes (1), by reacting with tri-isobutylaluminium, are dimerized selectively in a 'head-to-tail' fashion to conjugated tetraenes having different structures in relation to the different nature of the transition-metal complex.The preparative aspect of these induced reactions is discussed, and, in the light of previous reports, some mechanistic considerations are presented.

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