A Novel Friedel-Crafts Reaction of Hindered Ketones

Article abstract of DOI:10.1021/jo00191a026

Mesitylene has been shown to react with acetyl chloride in the presence of aluminium chloride to form 1,1-dimesitylethene.Acetomesitylene has been demonstrated to be an intermediate in the reaction, which proceeds in the second step by nucleophilic attack by the arene on the carbonyl group of acetomesitylene, which is activated by the formation of a polarized complex with aluminum chloride.Mesitylene reacts similarly with propionyl chloride, forming 1,1-dimesitylpropene; propiomesitylene is an intermediate.Steric and electronic factors responsible for this unique Friedel-Crafts reaction are discussed.