ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
On treatment with HSO3F in SO2C1F 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 [3-13C]-1a (1a*) and doubly labelled [1,3-13C2]-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.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19820650713
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