THERMAL FRAGMENTATION AND REARRANGEMENT OF BETA-KETOSULFIDE AND BETA-KETOSULFONE DERIVATIVES

Thermal fragmentation and rearrangement of neat phenacyl aryl sulfides I and II have been thoroughly investigated and found to involve cleav age of the C-S and C-C bonds followed by a series of ii-abstraction, c oupling, dimerization, rearrangement, and cyclization reactions. Also, in the presence of isoquinoline as a radical trap, I gave 1-phenyl- a nd 1-benzylisoquinoline in addition to the rearrangement products. Ana logous results, beside SO2 arylsulfonic acid and biaryl, were also obt ained on heating phenacyl aryl sulfones In and IV in tetraline. A suit able mechanism has been suggested to account for the isolated products .