ROLE OF SUBSTRATE AND MEDIA POLARITY ON THE STEREOCHEMISTRIES OF THE SE2 BROMINATION OF TRIALKYL-SEC-BUTYLTIN COMPOUNDS

Although electrophilic substitution at saturated carbon has been studied in some detail, 1 little is known about the factors governing the stereochemical consequences of such reactions. The earliest stereochemical studies at carbon-tin centers examined the reaction of halogens with cyclopropyl derivatives; retention of configuration at carbon was uniformly observed2-5but this was not unexpected because of the high inversion barrier. © 1979, American Chemical Society. All rights reserved.