Cycloadditions of thiocarbonyl ylides with N-sulfinylamines

✍ Scribed by Rolf Huisgen; Grzegorz Mloston; Kurt Polborn

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 239 KB
• Volume: 10
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1999)10:7<662::aid-hc23>3.0.co;2-y

✦ Synopsis

Thiobenzophenone S-methylide (6) and 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-methylide (17) were allowed to react with N-sulfinylaniline (7) and N-sulfinyltosylamide (8) furnishing 1,3,4-dithiazolidine 3-oxides. However, in the interaction 17 ‫ם‬ 8 the main product was the 1,2,4-oxadithiolane 2tosylimide (22); that is, the adduct to the S‫ס‬O bond. An X-ray analysis confirmed structure 22 and revealed an envelope conformation of the heteroring. A tentative interpretation considers a switching from the concerted addition to the N‫ס‬S bond of N-sulfinylamines to a two-step pathway via a zwitterion leading to 22.