Three-Membered Rings with Two Heteroatoms

This chapter discusses the synthesis, transformation, and decomposition of three-membered rings. The chapter reviews three classes of compounds—(1) oxaziridines, (2) diaziridines, and (3) diazirines. The synthesis, configurational stability, reactions, photochemical formation, and transformation of oxaziridines are described in the chapter. The application of new oxidizing reagents has led to new procedures of oxaziridine synthesis. Alkyl hydroperoxides in the presence of catalytic amounts of molybdenum compounds, the reagent of Halcon epoxidation, makes oxaziridines from Schiff bases in good yield. Simple reactions of oxaziridines, such as their behavior toward acids, bases, and ferrous salts are reviewed in the chapter. The chapter describes the synthesis and reactions of diaziridines. The reactions of two compounds of diaziridines—diaziridinones and diaziridinimines are also discussed. The chapter also discusses the preparation and reactions of diazirines, diazoalkane interconversion, and thermal and photolytic decomposition of diazirines. Fluorodiazirines that are compounds of diazirines are also described, which are obtained from suitable perfluorinated amines by reduction with ferrocene or iodide, as well as by reduction with diphenylamine, semicarbazide, hydrochloride, and by electrolytic reduction.