Isomerization of substituted biphenyls by superacid. A remarkable confluence of experiment and theory.
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.
Sherman
S Christopher
SC
School of Chemical Engineering, Georgia Institute of Technology, Atlanta, Georgia 30332-0100, USA.
Iretskii
Alexei V
AV
White
Mark G
MG
Gumienny
Charles
C
Tolbert
Laren M
LM
Schiraldi
David A
DA