A photo-induced rearrangement involving aryl participation (original) (raw)

OUR observation of a photo-induced Fries rearrangement3 prompted us to study the photochemistry of some of the expected primary products. For this reason we investigated the effect of ultraviolet light on alcoholic solutions of substituted phenacyl chlorides (I, Y = Cl). X-C6H1,-CCCH2Y (I) X-C6H4-CH2C02R (I I) Previous work3 led us to irradiate a 1% ethanolic solution of Ehydroxyphenacyl chloride (I, X = E-OH, Y = Cl). Within 2 hours, the carbonyl stretching frequencies of the starting material (1678, 1690 cm-l) disappeared and two new strong bands at 1671 and The former band was due to Lo-hydroxyacetophenone isolated as its 2:4_dinitrophenylhydrazone, m.p. band to ethyl-(e-hydroxyphenyl)-acetate (II, X = 1725 cm-1 were apparent.