Cycloaddition of phenyl azide to unsymmetrical azabicyclic alkenes

Autor: Djaballah Belkacemi, Gerald A. Griffith, John R. Malpass, Mark D. Robertson
Rok vydání: 2002
Předmět:
Zdroj: ARKIVOC, Vol 2002, Iss 6, Pp 164-174 (2002)
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0003.615
Popis: Addition of phenyl azide to selected derivatives of the 2-azabicyclo(2.2.1)hept-5-ene, 2- azabicyclo(2.2.1)hept-5-en-3-one and 2-azabicyclo(2.2.2)oct-5-en-3-one ring systems is described. Modest levels of regioselectivity are observed; 100% exo-facial selectivity is found in the (2.2.1) systems but exo- and endo- adducts are formed from the (2.2.2) substrate allowing isolation of all four possible stereoisomers. Photolytic removal of dinitrogen from the triazolines gives aziridines which are potential precursors to stereospecifically functionalised aziridino- cyclopentanes and aziridino-cyclohexanes.
Databáze: OpenAIRE