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A photo-induced rearrangement involving aryl participation

✍ Scribed by J.C. Anderson; C.B. Reese

Publisher: Elsevier Science
Year: 1962
Tongue: French
Weight: 190 KB
Volume: 3
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)62031-2

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✦ Synopsis

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 ultra-violet 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.

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