Thiadiaziridine 1,1-Dioxides: Synthesis and Chemistry

Article abstract of DOI:10.1021/jo00323a021

The synthesis and chemical reactions of a series of thiadiaziridine 1,1-dioxides (2) are described.The thermal stability is highly dependent on the R group and in one case (R = tert-octyl) is postulated that the thermolysis initially produces a diradical intermediate which can be trapped or further fragments to give a nitrene.A temperature-dependent NMR study on the coalescence of the diastereotopic α-methyl protons of 2b gives a ΔG^<*> = 20 kcal*mol^-1.