Novel Synthesis of 3-Thietanols by Reactions of 2-(1-Haloalkyl)oxiranes with Ammonium Thiocarbamate

Abstract

Reactions of 2- (1-haloalkyl) oidranes (1) with ammonium thiocarbamate (2) have been investigated. (RS) -2-E (RS) -α-Bromobenzylloxirane (la) with N-phenethylthiocarbamic acid phenethylammonium salt (2a) in methanol gave a N-phenethylthiocarbamate derivative (3a). Then, (3a) was treated with phenethylamine in DMSO to provide trans-2-phenyl-3-thietanol (4a) stereospecifically. Several other 3-thietanols (4b-d, 7, 12) were synthesized from the 2- (1-haloalkyl) oxiranes (1b-d, 6, 10) by the same procedure. These results demonstrate that this procedure is effective for synthesis of 3thietanols employing (2) as a sulfur source of 3-thietanols. A plausible mechanism of the 3-thietanol formation is presented.