1.01 - Aziridines and Azirines: Monocyclic

Add time:08/24/2019    Source:sciencedirect.com

A survey of the chemical literature published between 1995 and 2007 dealing with the chemical reactivity and synthesis of monocyclic aziridines and 2H-azirines is presented. The reactivity of monocyclic aziridines is discussed first, specifically including sections on nucleophilic ring-opening reactions, reactions of N-unsubstituted aziridines, rearrangement chemistry, radical reactions, [3+2] cycloadditions, [3+3] annelations, ring-expansion chemistry, metal-catalyzed reactions, and aziridinyl carbanion chemistry. The synthesis of monocyclic aziridines, covering both non-enantioselective and enantioselective methods, is reported. Examples describing the metal-catalyzed nitrenation of alkenes and the methylidenation of imines are outlined in some detail. The chemistry of 2H-azirines is dominated by processes in which the strain of the three-ring system is relieved. 2H-Azirines undergo reactions in which they can function as a nucleophile or as an electrophile. They can also participate in cycloaddition reactions as 2π-components and undergo selective cleavage of the ring when subjected to thermolysis or photolysis. This chapter includes more than 370 references taken from the recent literature.

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