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An analogue of the photo-fries rearrangement; the photolysis of vinyl benzoate.

✍ Scribed by R.A. Finnegan; A.W. Hagen

Publisher
Elsevier Science
Year
1963
Tongue
French
Weight
191 KB
Volume
4
Category
Article
ISSN
0040-4039

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✦ Synopsis

The classical Fries rearrangement, ' a well known acidcatalyzed process illustrated in equation 1, can be effected in 3-6 the absence of acid catalysts by means of ultraviolet light. OH (1) CsH,OCOR -------) COR + OH Esters successfully rearranged by the photo-Fries reaction include phenyl acetate3 (equation 1, R =CHs) and catechol acetate, 3 the para-tert-butylphenyl esters of a number of aromatic acids, 6 phenyl benzoate, 5 a number of variously substituted phenyl beneoate derivatives 4,5 and phenyl ferrocene carboxylate. 5 The structures of the products 3-6 indicate predominate, if not ex-Undergraduate research assistant supported by a grant from the Petroleum Research Fund (#710-A) administered by the American Chemical Society.

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