ELECTROCHEMICAL ADDITIONS OF THE ALLYL AND THE BENZYL GROUPS OF ALLYL AND BENZYL HALIDES TO ACETONE.

Article abstract of DOI:10.1246/bcsj.56.1791

Electrolysis of allyl chloride and five molar excess of acetone in hexamethylphosphoric triamide containing 0. 5 M tetrabutylammonium perchlorate gave an addition product, 2-methyl-4-penten-2-ol, in a 53% yield. Allyl groups of 1-chloro-2-methyl-2-propene, 1-chloro-2-butene(3), 3-chloro-1-butene(4), 1-chloro-3-methyl-2-butene(5), and 3-chloro-3-methyl-1-butene(6), and benzyl groups of benzyl chloride, benzyl bromide, and 1-chloro-1-phenylethane can similarly be added to acetone by electrolysis to give the corresponding alcohols in fair to good yields. Among these electrochemical reactions, those of 3, 4, 5 and 6 with acetone give respectively two isomeric homoallyl alcohols, one of the isomers is not accessible by the usual chemical reaction between allylic organometallics and acetone.