A convenient synthesis of 7-substituted norbornadienes
Abstract
Contrary to an earlier claim, reactions of (1) with m-chloroperbenzoic acid, N-bromosuccinimide, and N-chlorosuccinimide, give the diester (15) and the syn-norbornadienes (2), (4), and (6), respectively; reactions of (1) with lead tetra-acetate and iodine also proceed with retention of C-7 stereochemistry but with bromine and chlorine inversion at C-7 is increasingly dominant.