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Review | Regular issue | Vol 94, No. 11, 2017, pp.1997-2029
Published online, 14th September, 2017
DOI: 10.3987/REV-17-866
Oxidative Syntheses and Ring Opening of Oxazolines and Related Compounds by Ammonium Tribromide

Shinsei Sayama*

*Natural Sciences (Chemistry), Fukushima Medical University, Hikarigaoka, Fukushima, 960-1295, Japan

Abstract

Oxidative syntheses and ring opening of oxazolines and related compounds with trimethylphenylammonium tribromide (phenyltrimethylammonium tribromide, PTAB) or pyridinium hydrobromide perbromide (PHPB) were summarized. PTAB and PHPB were effective for respective syntheses of oxazolines, dihydrooxazines, and 6-bromobenzothiazoles. PTAB was also available for the conversion of oxiranes to dioxanes in the presence of 1,3-propanediol. The oxidative ring opening of furans, oxazolines, and dioxanes to respective furanones, cyanomethyl esters, and hydroxypropyl esters with PTAB or PHPB was also described.