98081-82-4Relevant articles and documents
Visible-light sensitization of vinyl azides by transition-metal photocatalysis
Farney, Elliot P.,Yoon, Tehshik P.
supporting information, p. 793 - 797 (2014/01/23)
Irradiation of vinyl and aryl azides with visible light in the presence of Ru photocatalysts results in the formation of reactive nitrenes, which can undergo a variety of C-N bond-forming reactions. The ability to use low-energy visible light instead of UV in the photochemical activation of azides avoids competitive photodecomposition processes that have long been a significant limitation on the synthetic use of these reactions. Rock and pyrrole: Irradiation of vinyl and aryl azides with visible light in the presence of Ru photocatalysts results in the formation of reactive nitrenes, which can undergo a variety of C-N bond-forming reactions. The ability to use low-energy visible light instead of UV in the photochemical activation of azides (see picture) avoids competitive photodecomposition processes. Copyright
Methyl 2-aryl-2H-azirine-3-carboxylates as dienophiles
Alves, M. Jose,Gilchrist, Thomas L.
, p. 299 - 303 (2007/10/03)
Diels-Alder reactions of the methyl 2-aryl-2H-azirine-3-carboxylates 1a and 1b have been investigated in order to determine the stereoselectivity and regioselectivity of the reaction. The azirines react with a range of electron rich dienes at room temperature to give Diels-Alder adducts. The reaction leads to the formation of endo-cycloadducts with both cyclic and acyclic dienes; furan Is exceptional in giving an exo-adduct 7. X-Ray crystallography has established the structure 9 of the Diels-Alder adduct formed from the azirine 1a and 1-acetoxybutadiene. The same regioselectivity, in which the more nucleophilic terminus of the diene combines with the carbon atom of the C=N bond, is found in the adducts from several other 1- and 2-substituted dienes. Only isoprene, among the dienes examined, gives a mixture containing the opposite regioisomer 14 as a minor component.
