Reactions ofN-sulfonylalkylamines with ynamines — formation of 2H-1,2-thiazete 1,1-dioxides, novel thioketeneS,S-dioxide dimers, and other s,n-heterocycles

✍ Scribed by Tornus, Ingo ;Schaumann, Ernst ;Mayer, Roland ;Adiwidjaja, Gunadi

• Book ID: 102904210
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 615 KB
• Volume: 1995
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.1995199510251

✦ Synopsis

Abstract

N‐Sulfonylalkylamines 2a, b react with ynamines 3 to give primarily 2__H__‐1,2‐thiazete 1,1‐dioxides 4. But, except for the 4‐triphenylsilyl species 4a, b, these products are unstable and undergo electrocyclic ring opening to very reactive amidinosulfenes 5, which are transformed into different products, depending on the ynamine substituents R^2^. The 1,3‐dithietane 1,1,3,3‐tetraoxide 8 is formed from N‐sulfonylisopropylamine (2a) and the trimethylsilyl‐substituted ynamine 3b via amidinosulfene 5c and probably thioketene S,S‐dioxide 7. On the other hand, (isopropylamidino)sulfene 5d dimerizes to the 2__H__‐1,5,2‐dithiazine 9 and also gives the [2 + 4] cycloadducts 10a, 11a by reaction with 2a and ynamine 3c, respectively. In contrast, it was possible to trap phenyl‐substituted amidinosulfenes 5e‐h by addition of water or methanol.