MECHANISMS OF ELIMINATION REACTIONS .26. POTASSIUM T-BUTOXIDE PROMOTED DEHYDROCHLORINATIONS OF ISOMERIC CHLORODIPHENYLETHENES

The isomeric chlorostilbenes have been subjected to potassium t-butoxide induced dehydrochlorination in t-butyl alcohol, in 5 M dimethyl sulfoxide in t-butyl alcohol, and in dimethyl sulfoxide (DMSO). The kinetics of these dehydrochlorinations were studied in the first two of these solvents, and competitive reactivities were measured in DMSO. In addition, the rates of potassium t-butoxide induced dehydrochlorination-rearrangement3 of 2-chloro-1,1-diphenylethene in 5 M DMSO-t-BuOH and in DMSO4 and a competition experiment with 1-chloro-cis-1,2-diphenylethene and 2-chloro-1,1-diphenylethene was performed in DMSO. The changes in reactivity ratios are discussed briefly. © 1969, American Chemical Society. All rights reserved.