41.2.3 Nitrosoalkanes and Nitroso Acetals (N,N-Dialkoxyamines) (Update 2026)

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Abstract Nitrosoalkanes and nitroso acetals (N,N-dialkoxyamines) have emerged as highly versatile intermediates in modern organic synthesis, despite their intrinsic instability and tendency toward tautomerization and dimerization. This review provides an updated and comprehensive overview of their synthesis, reactivity, and applications. Recent advances include continuous-flow methodologies that enhance safety and efficiency, as well as innovative strategies for in situ generation to overcome instability issues. Synthetic approaches encompass substitution, addition, oxidation, and rearrangement reactions, enabling access to geminal chloronitroso compounds, metal-coordinated nitrosoalkanes, and structurally diverse nitroso acetals. Tandem and cascade processes have gained prominence for rapidly increasing molecular complexity with excellent regio- and stereocontrol, including catalytic asymmetric variants. Applications extend beyond classical transformations, such as oxidation to nitroalkanes, reduction to amines, and heterocycle formation via cycloaddition reactions, to cutting-edge uses in polymer synthesis, radical-mediated processes, and the functionalization of nitrosoalkane-metal complexes for C—H activation and alkene exchange. These developments underscore the growing role of nitroso compounds as strategic building blocks for complex architectures, biologically active molecules, and advanced materials, reinforcing their importance in contemporary synthetic chemistry.

Ce résumé expose les affirmations des auteurs. BNTIC ne l’interprète pas comme une validation indépendante des résultats.