Allenes. Part XXIII. Mechanistic studies on the formation of 1-bromoallenes from prop-1-yn-3-ols
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 13,p. 1995-1998
- https://doi.org/10.1039/p29720001995
Abstract
The formation of 1-bromo-3-methylpenta-1,2-diene by the action of hydrobromic acid on 3-methylpent-1-yn-3-ol in the presence of cuprous bromide has been investigated in the temperature range 0–25° and found to follow first-order kinetics. The rate constant and half-life at 0·00, 20·80, and 25·20° and the activation energy for the reaction have been determined. Evidence has been obtained to support the intermediacy of an acetylene–copper(I)π-complex from which the 1 -bromoallene is formed by a stereospecific SNi′ process in which the configuration is retained.Keywords
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