Premium
Reactions of N ‐sulfonylalkylamines with ynamines — formation of 2 H ‐1,2‐thiazete 1,1‐dioxides, novel thioketene S , S ‐dioxide dimers, and other s,n‐heterocycles
Author(s) -
Tornus Ingo,
Schaumann Ernst,
Mayer Roland,
Adiwidjaja Gunadi
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199510251
Subject(s) - chemistry , methanol , medicinal chemistry , trimethylsilyl , ring (chemistry) , organic chemistry
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.