Functionalization of olefins by alkoximidoylnitrenes

Journal Article · Fri Aug 04 00:00:00 EDT 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00277a037· OSTI ID:7196847

Subbaraj, A; Rao, O S; Lwowski, W ^[1]

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1. New Mexico State Univ., Las Cruces (USA)

(N-Cyano- and N-(methylsulfonyl)alkoxycarbimidoyl)nitrenes, generated in situ from the corresponding azides by 300-nm UV light, convert a variety of olefins cleanly and stereospecifically to the corresponding aziridines. These can readily be hydrolyzed to N-unsubstituted aziridines or ring-opened to allylic isoureas. The nitrenes can also be generated by thermolysis at 80{degree}C. The azides add to norbornene to give triazolines, which lose nitrogen to give the exo-aziridines.

• OSTI ID: 7196847
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:16; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
AROMATICS
AZAARENES
DATA
DATA ANALYSIS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
SYNTHESIS