Functionalization of olefins by alkoximidoylnitrenes

Functionalization of olefins by alkoximidoylnitrenes

(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...

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Veröffentlicht in:Journal of organic chemistry 1989-08, Vol.54 (16), p.3945-3952
Hauptverfasser: Subbaraj, A, Rao, O. Subba, Lwowski, Walter
Format: Artikel
Sprache:eng
Schlagworte:
400201 - Chemical & Physicochemical Properties
Aliphatic compounds
AROMATICS
AZAARENES
Chemistry
DATA
DATA ANALYSIS
Exact sciences and technology
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
INFORMATION
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
MEASURING INSTRUMENTS
MEASURING METHODS
NUMERICAL DATA
Organic chemistry
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
Preparations and properties
SYNTHESIS
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Beschreibung
Zusammenfassung:(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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00277a037