Oxidation of 1,4-dihydro-1,4-diphenyl-2,3-benzodithiin

✍ Scribed by Ryu Sato; Eiji Takeda; Shiduko Nakajo; Takeshi Kimura; Satoshi Ogawa; Yasushi Kawai

• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 170 KB
• Volume: 12
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.1034

✦ Synopsis

Abstract

1,4‐Dihydro‐1,4‐diphenyl‐2,3‐benzodithiin (3), synthesized from 1,2‐bis(phenylmethyl)benzene (1), was subjected to oxidation to give 1,4‐dihydro‐1,4‐diphenyl‐2,3‐benzodithiin 2‐oxide (4) as a mixture of diastereomers separable by column chromatography. (1R*,2R*,4S*)‐1,4‐Dihydro‐1,4‐diphenyl‐2,3‐benzodithiin 2‐oxide (4‐meso‐1) was obtained preferentially from (1R*,4S*)‐1,4‐dihydro‐1,4‐diphenyl‐2,3‐benzodithiin (3‐meso) with m‐chloroperbenzoic acid (m‐CPBA). The 4‐meso‐1 stereoisomer afforded an unexpected product 1,3‐diphenylbenzo[c]thiophene (5) upon further oxidation with mCPBA. On the other hand, oxidation of 1,4‐dihydro‐1,4‐diphenyl‐2,3‐benzodithiin 2‐oxides (4‐dl and 4‐meso), with Oxone gave 1,4‐dihydro‐1,4‐diphenyl‐2,3‐benzodithiin 2,2‐dioxide (7). © 2001 John Wiley & Sons, Inc. Heteroatom Chem 12:209–216, 2001