Aromatization of Arene 1,2-Oxides. 1-(Trimethylsilyl)benzene 1,2-Oxide

Article abstract of DOI:10.1021/jo00322a014

Aromatization of 1-(trimethylsilyl)benzene 1,2-oxide (1) affords a mixture of o-(trimethylsilyl)phenol and phenol, the ratio of which is pH dependent.Aromatization of <5-(2)H>-1-(trimethylsilyl)benzene 1,2-oxide gave the following results. (1) At pH 1.1 or 7 all the deuterium label in o-(trimethylsilyl)phenol was para to the hydroxyl group. (2) At pH 1.1 the phenol formed was exclusively <4-(2)H>phenol, but at pH 7 it was 70-75percent <4-(2)H>phenol and 25-30percent <3-(2)H>phenol.The pathway of the aromatization reaction is discussed.