Aromatization of arene 1, 2-oxides. 1-(Trimethylsilyl) benzene 1, 2-oxide

…, DR Boyd, GA Berchtold

Index: Epp, James E. Van; Boyd, Derek R.; Berchtold, Glenn A. Journal of Organic Chemistry, 1981 , vol. 46, # 9 p. 1817 - 1820

Full Text: HTML

Citation Number: 11

Abstract

Aromatization of 1-(trimethylsily1) benzene 1, 2-oxide (1) affords a mixture of o- (trimethylsiiy1) phenol and phenol, the ratio of which is pH dependent. Aromatization of [5- 2H]-l-(trimethyLsilyi) bene l, 2-oxide gave the following results.(1) At pH 1.1 or 7 all the deuterium label in o-(trimethylsily1) phenol was para to the hydroxyl group.(2) At pH 1.1 the phenol formed was exclusively [4-2H] phenol, but at pH 7 it was 70-75%[4-2H] phenol and ...