ISSN:
0947-3440
Keywords:
[2 + 2] Cycloadditions
;
2H-1,2-Thiazete 1,1-dioxides
;
Amidinosulfenes, in situ formation of
;
Diaminothioketene S,S-dioxide
;
1,3-Dithietane 1,1,3,3-tetraoxide
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
N-Sulfonylalkylamines 2a, b react with ynamines 3 to give primarily 2H-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 R2. 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 2H-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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199510251
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