Abstract

The neighboring-group effect is not caused by the electron-donor center itself, but probably by the metal atom bound to it in an intermediate such as 1. The result of the effect is that α or β donor substituents (OH, OMe, NC) in vinyl bromides (for example 2) strongly accelerate the alkylating substitution reaction with alkyl transition-metal reagents like Me4MnLi2. The more pronounced effect of α substituents is also in agreement with the proposed intermediate 1 (n = 0), because five-membered rings are known to form more readily than six-membered rings. [M] = Fe or Mn complex fragments.

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