Journal of Organic Chemistry p. 3967 - 3970 (1984)
Update date:2022-08-11
Topics:
Covey, William D.
DeHaan, Franklin P.
Delker, Gerald L.
Dawson, Steven F.
Kilpatrick, Peter K.
et al.
Kinetic studies have been made of the AlCl3-catalyzed reaction of phenylmethanesulfonyl chloride with benzene or toluene in nitromethane at 20 deg C.The reaction follows first-order dependence upon phenylmethanesulfonyl chloride and catalyst but zero-order dependence upon aromatic hydrocarbon.It is proposed that the reaction involves a benzyl cation which is formed in situ.Competitive results are also reported for the reaction with (p-chlorophenyl)methanesulfonyl chloride.In both cases, the relative reactivities, kT/kB, and toluene isomer product distributions appear to be exceptions to Brown's selectivity relationship.
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