Chapter 1 - Compounds with three- and four-membered heterocyclic rings

Abstract

A number of novel routes to three- and four-membered heterocycles are presented in this chapter. Several related species are identified as intermediates in the formation of other heterocycles. A number of properties and reactions of oxiranes appear under the various headings concerned with epoxides. Also, the preparation and properties of arene oxides are reviewed. The chapter discusses the photolysis of di-n-butylmalonylperoxide involving photodecarboxylation to produce an α-lactone intermediate. “Alkoxide trap” is described as a system less prone to act as a leaving group but which retains an electrophilic multiple bond. Aziridines are used as biological alkylating and anticancer agents. The significant difference between the steric hindrance of the R and Ph groups influences the reaction between oximes and Grignard reagents to yield aziridines. Later, the dioxirane is investigated by mass spectrometry and microwave spectroscopy. The synthesis and chemical properties of four-membered rings with one sulfur atom, such as thietanes (trimethyl sulfides), thietes or thietenes, thietanones, four-membered rings containing one nitrogen atom, such as azetidines (trimethyleneamines), azetidinones; oxoazetidines, azetines, and azetes are also analyzed in the chapter.