- A-new synthesis of N-sulfinylamines via β-elimination of chloroform from trichloromethanesulfinamides
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The synthesis of various N-monosubstituted trichloromethanesulfinamides by two alternative and novel procedures is described. All these compounds have been found to undergo base-induced elimination of chloroform with formation of the corresponding N-sulfinylamines. Reaction proceeds smoothly under mild conditions.
- Braverman, Samuel,Cherkinsky, Marina
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p. 487 - 490
(2007/10/03)
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- Thiaziridine 1,1-Dioxides
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Experiments towards a 1,3-elimination of hydrogen halides from α-chlorosulfonamides, α-bromosulfonamides, and N-chlorosulfonamides did not yield isolable thiaziridine 1,1-dioxides 4.Therefore, at -78 deg C, the diazoalkanes 10 were allowed to react with N-sulfonylamines 14 generated in situ by hydrogen chloride elimination from sulfamoylchlorides with triethylamine.If the work-up temperature was kept below -30 deg C, from tert-alkyldiazomethanes and tert-alkylsulfamoylchlorides the 2,3-di-tert-alkylthiaziridine 1,1-dioxides 4f - i were obtained in 32 - 47 percent yield.They form colorless, thermally labile crystals.Their structure was based on IR, UV and 1H-NMR spectra as well as on the quantitative thermal decomposition into sulfur dioxide and aldimines.The disubstituted diazomethanes 23 reacted with tert-butylsulfonylamine affording, besides N-tert-butylketimines (the decomposition products of intermediate trisubstituted thiaziridine 1,1-dioxides 21), tert-butylsulfinylamine 25 and ketones 26.The latter products presumably resulted from the cheletropic decomposition of the oxathiiranes 24.
- Quast, Helmut,Kees, Frieder
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p. 774 - 786
(2007/10/02)
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