Benzylation of Allylbenzene. Formation of 3,4-Diphenyl-1-butene and 3-Benzyl-3,4-diphenyl-1-butene

Abstract

Abstract When allylbenzene was treated with the same moles of sodium amide and benzyl chloride in liquid ammonia, one or two benzyl radicals were introduced into allylbenzene to produce 3,4-diphenyl-1-butene and 3-benzyl-1-butene. The reaction is similar to the well-known reaction of benzyl cyanide and benzyl chloride in liquid ammonia and that of 2-phenyl-1-ethanol and benzyl chloride in benzene. Two forms of 2,3-diphenylpropionic acid were isolated and their I. R. spectra were measured. Different curves were obtained in KBr disks, while the identical curves were obtained carbon tetrachloride solution. Infrared absorption spectra were measured by Professor Kinumaki and his associates of this Institute and the elementary analyses were performed in the laboratory of Shionogi and Company, Ltd., to whom the writers are deeply indebted.