The catalytic action of anionic catalysts. Part XII. Reaction of n-butyl-lithium, ethyl-lithium, and phenyl-lithium with 1,1-diphenylethylene in ether solvents

Abstract

In the reaction of 1,1-diphenylethylene with n-butyl-lithium, ethyl-lithium, and phenyl-lithium in diethyl ether–benzene as solvent, and with n-butyl-lithium in tetrahydrofuran, the order of reaction is unity in the olefin but is of a fractional order in the organolithium compound: ½ for n-butyl-lithium and ¼ for ethyl-lithium in 0·4% Et2O–benzene; 1/2·4 for phenyl-lithium in 4% Et2O–benzene; and ½ for n-butyl-lithium in 100% tetrahydrofuran.Our previous results in 100% benzene as solvent gave the orders: 1/6 for n-butyl lithium and 1/9 for ethyl-lithium. Thus the increase in polarity of the solvent has reduced the extent of aggregation of the metal alkyl.