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DOI: 10.1055/sos-SD-047-00322

Kostikov, R. R.; Khlebnikov, A. F.; Sokolov, V. V.Science of Synthesis, (201047848.

Although the synthesis of alkenes by deamination of aziridines has been mentioned in HoubenWeyl, Vol. 5/1b, p 753 and in a review,[‌203‌] one cannot consider this method as being convenient and general. In most cases, aziridines are much less readily available than the corresponding simple alkenes. However, since alkylaziridines with free NH groups can be prepared from alkenes with inversion of the original alkene configuration, and the subsequent deamination can be achieved with retention, the overall process provides an alkene with inverted configuration.[‌203‌] For such deamination protocols, nitrosyl chloride and alkyl nitrites (with cheletropic extrusion of nitrous oxide) or the not so easily available difluoroamine (via N-nitrenes with loss of nitrogen) have been proposed. For an analogous isodiazene process, the oxidation of N-aminoaziridines 142 with manganese(IV) oxide, nickel(II) peroxide, or tert-butyl hypochlorite has been described; in some cases, the intermediary 3,4-dihydro-1,2-diazetes 144 can be isolated along with the alkenes 143 (Scheme 53).[‌203‌,‌323‌]

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