THE EFFECT OF ALKYL-GROUPS ON CARBANION STABILITY .1. INTERACTION OF SMALL RINGS WITH ADJACENT CARBANION CENTERS


BALCIOGLU N., SEVIN F., EVIN O., PEYNIRCIOGLU N.

BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, cilt.96, sa.2, ss.139-142, 1992 (SCI-Expanded) identifier

Özet

Relative kinetic acidity measurements have shown that the cyclobutyl group has the ability to stabilize an adjacent carbanion center similar to vinyl and cyclopropyl groups, although to a lesser extent. The results of semiempirical calculations (MNDO) covering all the mentioned substituents, including the isopropyl group correlate well with the experimentally determined relative kinetic acidities.