Organic Chemistry Portal
Chemicals >> Oxidizing Agents

Nitrous Oxide, N2O

Nitrous oxide is an O atom transfer reagent, that is relatively nontoxic (laughing gas). Due to its low reactivity, selective oxidation reactions of highly reactive compounds are possible. Nitrous oxide can also serve as an N atom donor.

Recent Literature

A catalytic synthesis of cycloalkanols in the presence of N2O as an oxygen transfer agent onto sp3-hybridized carbons of simple precursors offers mild conditions and wide substrate scope. The reaction even enables to access carbocyclic compounds in an enantioselective manner.
S. Ni, F. Le Vaillant, A. Mateos-Calbet, R. Martin, J. Cornella, J. Am. Chem. Soc., 2022, 144, 18223-18228.

A redox cyclization of amides and sulfonamides with nitrous oxide enables a direct and simple synthesis of heterocycles. Various amides and sulfonamides could undergo directed ortho metalation (DoM) by treatment with BuLi, and the lithium intermediate can be trapped by N2O gas to achieve redox cyclization.
Z. Lai, C. Wang, J. Li, S. Cui, Org. Lett., 2020, 22, 2017-2021.