Generation and cyclization of thiocarbonyl S-ylides by reaction of diazocompounds with C-sulfonyldithioformates

✍ Scribed by Ahmed F. Khattab; Omar M. Ali; Ibrahim El-Sayed

• Publisher: John Wiley and Sons
• Year: 2007
• Tongue: English
• Weight: 164 KB
• Volume: 18
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20246

✦ Synopsis

Abstract

The unexpected 1,3‐benzodithiine derivatives 5b,c were obtained from the reactions of trimethylsilyldiazomethane 2 with C‐sulfonyldithioformates, bearing pentachlorophenylthio group, 1b,c via unprecedented cyclization of the transient thiocarbonyl ylides 4b,c. While the corresponding reaction with C‐sulfonyldithioformates, bearing phenylthio group, afforded 5a via [2 + 3]‐cycloadditive dimerization of a transient thiocarbonyl ylides 4a. Under the same reaction condition, C‐sulfonyldithioformates 1d–f react with diazomethane and/or phenyldiazomethane to afford the unsymmetrical 1,3‐dithiolane 7d,e and thiirane 8e,f derivatives, respectively. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:28–33, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20246