HETEROGENEITY AS A FACTOR IN THE ALKYLATION OF AMBIDENT ANIONS:PHENOXIDE IONS1'2

摘要

Sodium and potassium salts of phenol and p-tert-octylphenol have been alkylated with benzyl and allyl halides in a variety of solvents. Quanti¬tative yields of the ether (oxygen alkylation) are obtained whenever the reaction is conducted in solution. In addition, it is demonstrated that the truly heterogeneous reaction gives exclusively carbon alkylation* Reactions carried out with the phenolic salt present as a solid phase ordinarily give both carbon and oxygen alkylation, but this result is clearly a consequence of incursion by the homogeneous process. The factors, other than heterogeneity, which may influence the course of phenoxide alkylations are briefly discussed. An explanation is offered for the fact that heterogeneity confers an essentially irresistible preference for carbon alkylation.