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

✍ Scribed by Daniel Berner; D. Philip Cox; Hans Dahn

Publisher
John Wiley and Sons
Year
1982
Tongue
German
Weight
535 KB
Volume
65
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 the reaction at low temperature in an NMR. spectrometer, the formation of intermediates and side products was demonstrated.

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