Accession Number : AD0700004

Title :   REACTION OF CHROMYL CHLORIDE WITH SOME OLEFINS. II. THE OXIDATION OF TETRAARYLETHYLENES,

Corporate Author : QUEEN'S UNIV KINGSTON (ONTARIO)

Personal Author(s) : Gatzke,A. L. ; Stairs,R. A. ; Diaper,D. G. M.

Report Date : 16 JUL 1968

Pagination or Media Count : 8

Abstract : Chromyl chloride oxidation of tetraphenylethylene results in a novel cyclization reaction giving 9,10-diphenylphenanthrene in high yield. Some cyclization between geminal phenyl groups and cleavage of the olefinic bond occurs as evidenced by the presence of fluorenone and benzophenone as minor products. Polynuclear hydrocarbons such as 1,1'-binaphthyl and o-terphenyl which can be cyclized by Lewis acids are unreactive towards chromyl chloride. The observation of rotation about the central bond of a substituted tetraphenylethylene and of retardation of cyclization by substituent chlorine suggest that the oxidative cyclization proceeds by initial electrophilic attack at the olefinic bond to give a carbonium ion. (Author)

Descriptors :   (*ETHYLENES, *OXIDATION), (*CHROMIUM COMPOUNDS, *OXIDATION REDUCTION REACTIONS), CHLORIDES, PHENANTHRENES, CANADA

Subject Categories : Organic Chemistry

Distribution Statement : APPROVED FOR PUBLIC RELEASE