Photochemical reactions of tribenzyl borates in bromobenzene

Abstract

The u.v. light-induced reaction of tribenzyl borate in bromobenzene followed by hydrolysis of the product gives dibenzyl ether (27·5%), benzyl bromide (29·5%), benzaldehyde (25%), and benzene. Similarly, the irradiation of tris-1-phenylethyl borate in bromobenzene gives bis-1-phenylethyl ether, 1-phenylethyl bromide, acetophenone, p-dibromobenzene, and benzene. A possible reaction pathway for the formation of the ethers is discussed.