ChemInform Abstract: Oxidative and Reductive Generation of Reactive Organic Nitrogen Species and Their Synthetic Application

Abstract

Studies on reactive intermediates are important to clarify reaction mechanisms and also to design useful synthetic reactions. From this viewpoint, the generation of reactive nitrogen species and their synthetic application were studied using chemical and electrochemical oxidation and reduction. This article is organized under the following headings.1. Introduction2. Generation of Reactive Nitrogen Species by N-Halogenation Followed by Dehalogenation and Their Synthetic Application2.1. Rearrangement of N-Alkylhaloamidines2.2. Synthesis of 1, 2, 4-Oxadiazoles2.3. Synthesis of N-Imidoylsulfilimines2. 4. Synthesis of Δ4-1, 2, 4-Thiadiazolines3. Generation of Nitrenes by Electrochemical Reduction of N, N-Dihalo Compounds4. Electrochemical Generation of Reactive Nitrogen Species and Their Synthetic Application4.1. Ammoniumyl and Aminyl Radicals4.2. Nitrenes4.3. Aminonitrenes 4.4. Nitrenium Ions 4.5. Reactive Aminyl Anions4.6. Others 5. Concluding Remarks