On the migration of a carboxyl group in a Wagner-Meerwein rearrangement in superacid solution: proof by double labeling with carbon-13.

D Berner, DP Cox, H Dahn

Index: Berner,D.; Cox,D.P.; Dahn,H. Journal of the American Chemical Society, 1982 , vol. 104, p. 2631

Full Text: HTML

Citation Number: 18

Abstract

1, 2 Shifts of electron-withdrawing groups (COR, COOR,'COSR, CONR,, PO (OR),, etc.) toward electron-deficient centers have been observed in several carbenium ion rearrangements, including the pinacol,, glycidic ester, 3~ emipinacol,~ dienonephen01,~ and Wagner-Meerwein We have recently shown by double labeling with I3C that the P- hydroxy esters 1 (b, R= Me; c, R= Et) undergo Wagner-Meerwein