Conformational studies by dynamic NMR. part 36. : The steric barrier and the π-barrier to rotation in simple enamines: diethylaminocyclohexenes

Abstract

1-Diethylaminocyclohexene adopts a near-to-coplanar conformation at the N-Csp 2bond with a 5.95 Kcal mol π-barrier to rotation through an orthogonal conformation with the lone pair in the π-p1ane. In contrast 1-diethy1aim no-2-methylcyclohexene adopts a non-planar conformation with the lone-pair near to the π-p1ane and a steric barrier to rotation of the diethylamino group through the plane, of 8.1 Kcal mol .