98081-82-4Relevant academic research and scientific papers
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.
The photochemistry of α-azidocinnamates - A reinvestigation
Meth-Cohn, Otto,Williams, Nicola J. R.,MacKinnon, Angus,Howard, Judith A. K.
, p. 9837 - 9848 (2007/10/03)
α-Azidocinnamates have been reported elsewhere to yield one diastereomer of a trimer in a stepwise and efficient manner by photolysis using quartz equipment. We find that use of pyrex filters or ketone sensitisation instead of quartz leads to high yields of the presumed intermediate diastereomeric pair of aziridinoimidazoline dimers, as does brief irradiation in quartz. These dimers have been characterised by spectral and crystallographic methods, and shown to oxidise with DDQ to give imidazoledicarboxylic esters, while the action of base on both dimer diastereomers leads to one rearranged dimer, a 1,2-dihydropyrimidine. Surprisingly, only a mixture of both diastereomeric dimers gives the trimer on further photolysis.
