The Etard reaction. IV. Oxidation of ethylbenzene with chromyl chloride.
Rentea, C. N.; Rentea, Marina; Necsoiu, Ileana; Nenitzescu, C. D.
Inst. Org. Chem., Bucharest, Rom. Revue Roumaine de Chimie (1967),
12(12), 1495-501. CODEN: RRCHAX ISSN: 0035-3930. Journal written in
English. CAN 69:2591 AN 1968:402591 CAPLUS
Abstract
The Etard complex of ethylbenzene (I) was prepd. in CCl4 at 0°. Decompn. of the Etard complex of I by water yielded
phenylacetaldehyde (II) and acetophenone (III) in equal proportions, along with styrene and BzH. The same products were obtained by treatment of
styrene with chromyl chloride and hydrolysis of the complex, II being the major product. Chromyl chloride oxidn. of epoxyphenylethane yielded BzH and
II and a trace of III. Presumably all these compds. result from a common intermediate possessing an epoxide-like structure. The mechanism of these
reactions is discussed. |