Unusual stereochemical consequences during the substitution of V-shaped diaryl derivatives
Abstract
The benzylic bromination of diquinoline derivative 1 proceeds in a regio- and stereo-selective manner to yield exo,exo-dibromide 2, whose subsequent hydrolysis to a diol product takes place with retention of configuration as demonstrated by the X-ray structure of 3·H2O. Related V-shaped diaryl systems behave in a similar manner, and the unusual stereochemistry of these reactions is discussed and explained.