Benzyn-Zwischenprodukte in der nukleophilen aromatischen Substitution

Abstract

Many substitution reactions of aromatic halides, such as amination with metallic amides in ammonia or amine solutions, high-temperature alkaline hydrolyses and arylation with phenyllithium, lead to the formation of rearrangement products as the result of a common reaction path involving unstable 'benzyne' intermediates. The chemical evidence in favor of this reaction mechanism is discussed as are correlations of observed product compositions and applications to practical synthetic procedures.

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