The Di-π-methane rearrangement of 1,3,3-Triaryl-3-methoxyprop-1-enes

Abstract

A series of 1,3,3-triaryl-3-methoxyprop-1-enes has been synthesized to study the effects of substituents on the migratory aptitudes of aryl groups in the di- π-methane rearrangement leading to methoxy cyclopropanes. In most cases little specificity was found. 3-Aryl-3-methoxy-l,3-diphenylpropenes formed both c-2-aryl-r-1-methoxy-1,t-3-diphenylcyclopropane and I-aryl-r-1-methoxy-t-2,c-3-di- phenylcyclopropane while, with one exception, 1-aryl-3-methoxy-3,3-diphenylprop-1-ene yielded t-2-aryl-r-1-methoxy-l,c-3-diphenylcyclopropane. The rate of rearrangement of 1-aryl-3-methoxy- 3,3-diphenylprop-1-enes, with the exception of the p-methoxyphenyl compound (4d), which does not react, has been found to be almost invariant of the substituent in the aryl group.