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Influence of enol acetylation on the photo-fries rearrangement of anortho-acylaryl benzoate

✍ Scribed by Garcia, Hermenegildo ;Miranda, Miguel A. ;Roquet-Jalmar, Maria F. ;Martinez-Utrilla, Roberto

Publisher
John Wiley and Sons
Year
1982
Tongue
English
Weight
316 KB
Volume
1982
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The enol acetate 1b undergoes benzoyl‐oxygen bond rupture upon irradiation, giving a mixture of benzophenones 4 and 5. The primary photo‐Fries products 2 and 3 could not be isolated, due to a rapid intramolecular transacetylation. The acetophenone 6 rearranges to give the benzophenones 7 and 8 under the same conditions, but the yields are significantly lower than in the former case. Compounds 7 and 8 are separately correlated with 4 and 5 by treatment with acetic anhydride in the presence of pyridine.

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## Abstract Enol‐esters 1a‐1e undergo clean Photo‐__Fries__‐rearrangements without side reactions. With anthroyl derivatives the reaction is observed only at 254 nm, not at 366 nm.