1, 2??Shift of a Carboxyl Group in a Wagner??Meerwein Rearrangement

D Berner, DP Cox, H Dahn

Index: Berner, Daniel; Cox, D. Philip; Dahn, Hans Helvetica Chimica Acta, 1982 , vol. 65, # 7 p. 2061 - 2070

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Citation Number: 5

Abstract

Abstract On treatment with HSO 3 F in SO 2 C1F at 0, 3-hydroxy-2, 2-dimethyl-3-phenyl- propionic acid (1a) is transformed into 2-phenyl-3-methyl-2-butenoic acid (2a)(isolated yield: 40–44%). Using monolabelled [3-13 C]-1a (1a*) and doubly labelled [1, 3-13 C 2]-1a (1a**), the migration of HOOC (or a mechanistically equivalent group) was proved; a cross experiment established the intramolecular character of the rearrangement. By following ...