Metal catalysis in organic reactions. Part 9. Iron-induced reaction of organoaluminium compounds with aliphatic alk-1-ynes

Abstract

The reaction between trialkylaluminium compounds and aliphatic alk-1-ynes in the presence of catalytic amounts of iron trichloride has been studied under various experimental conditions. The reaction affords a complex mixture of products, the main components being essentially 2-alkylalk-1-enes and trialkylbuta-1,3-dienes; linear oligomers and cyclo-trimers are also recovered under suitable experimental conditions. The use of (S)-3-methylpent-1-yne gives rise to optically active products in high optical yields. The mechanism of the reaction is discussed and tentatively interpreted in terms of alkyliron intermediates.