Electrosynthesis of sulfur-containing organic compounds from cumulene derivatives using a sacrificial sulfur-graphite electrode

✍ Scribed by Akira Kunugi; Kimiko Kuwamura; Hidemitsu Uno

• Publisher: Elsevier Science
• Year: 1997
• Tongue: English
• Weight: 683 KB
• Volume: 42
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/s0013-4686(96)00430-6

✦ Synopsis

Electrosynthesis of sulfur-containing organic compounds from cumulene derivatives was studied using a sacrificial sulfur-graphite electrode.

1, I -Di-p-chlorophenyl-4.4-diphenylbuta-1,2.3-triene (la).

I. 1 -di-p-chlorophenyl-4,4-di-p-methylphenylbuta-1,2,3-triene

and I, I -di-p-methoxyphenyl-4,4-diphenylbuta-1,2,3-triene (Id) were used as cumulenes. With la, lb and lc, 7-membered ring compounds with five sulfur atoms such as pentathiepins Za, 2b and 2c were produced as the major products accompanied with dimeric compounds 3a, 3b and 3c which had a 1,2,5.6-tetrathiocin skeleton in minor amounts, respectively. However, Id, which is the most difficult to be reduced among the cumulenes studied, did not give sulfur-containing organic compounds. Yields of 2a, 2b and 2c decreased a little by the addition of a proton donor such as benzoic acid. Main products 2 will be initiated by a Michael addition of the polysulfide anion(s) ($ and/or !Z$) produced by electroreduction of elemental sulfur. By-products 3 will be probably produced by further reaction of 2 with the polysulfide anion(s). ("