78077-07-3Relevant academic research and scientific papers
Thiaziridine 1,1-Dioxides
Quast, Helmut,Kees, Frieder
, p. 774 - 786 (2007/10/02)
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.
