Thiadiaziridine 1, 1-dioxides: synthesis and chemistry

JW Timberlake, J Alender, AW Garner…

Index: Timberlake, Jack W.; Alender, Jeff; Garner, Archie W.; Hodges, Melvin L.; Oezmeral, Cenan; et al. Journal of Organic Chemistry, 1981 , vol. 46, # 10 p. 2082 - 2089

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Citation Number: 38

Abstract

The synthesis and chemical reactions of a series of thiadiaziridine 1, l-dioxides (2) are described. The thermal stability is highly dependent on the R group and in one case (R= tert- octyl) it 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 a-methyl protons of 2b gives a AG*= 20 kcal mol-'.