Organoaluminium compounds. VIII. The reactions of organoaluminium hydrides with phenylacetylene

Abstract

Organoaluminium hydrides react with phenylacetylene under mild conditions to give various products resulting either from substitution (metallation) of the acetylenic hydrogen or mono-addition or di-addition across the triple bond. The alkyl groups of dimethyl- and diethylaluminium hydrides take little or no part in the reaction, but in the case of diphenylaluminium hydride reaction of both hydride and phenyl groups can occur. In the presence of triethylamine the addition reaction between diphenylaluminium hydride and phenylacetylene is completely suppressed, and a mixture of the two possible substitution products is obtained.