Journal of the Chemical Society. Perkin transactions I p. 1900 - 1908 (1981)
Update date:2022-08-05
Topics:
Caporusso, Anna Maria
Giacomelly, Giampaolo
Lardicci, Luciano
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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Doi:10.1021/jo01105a623
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