Isomerization of substituted biphenyls by superacid. A remarkable confluence of experiment and theory

J Org Chem. 2002 Apr 5;67(7):2034-41. doi: 10.1021/jo0106445.

Abstract

Acid-catalyzed isomerization of dimethylbiphenyls is determined by the relative stability of intermediate carbocations, rather than the neutral products, and may be predicted by a simple semiempirical method (AM1). A general kinetic model for such isomerizations is suggested in which the rearrangement of an intermediate cation is the rate-limiting step. Control of regiochemistry of dialkylbiphenyls provides a useful entry into high-purity monomers for high-polymer synthesis.