110835-94-4Relevant academic research and scientific papers
Novel photoreactions of 2-Aza-1,4-dienes in the triplet excited state and via radical-cation intermediates. 2-Aza-di-π-methane rearrangements yielding cyclopropylimines and N-vinylaziridines
Armesto, Diego,Caballero, Olga,Ortiz, Maria J.,Agarrabeitia, Antonia R.,Martin-Fontecha, Mar,Torres, M. Rosario
, p. 6661 - 6671 (2007/10/03)
Triplet-sensitized irradiation of 2-aza-1,4-dienes affords N-cyclopropylimines via 2-aza-di-π-methane (2-ADPM) rearrangement pathways. In the case of the pentaphenyl-substituted azadiene 1, irradiation leads to formation of cyclopropylimine 2 as well as N-vinylaziridine 3. The transformations represent the first examples of di-π-methane rearrangement reactions that yield three-membered heterocyclic products. SET-sensitized irradiation of 2-aza-1,4-dienes, by using 9,10-dicyanoanthracene (DCA) as an electron-acceptor sensitizer and biphenyl as cosensitizer, brings about regioselective formation of N-vinylaziridines. Under these conditions, azadiene 1 also affords cyclopropylimine 37, resulting from an aryl-di-π-methane rearrangement. This result demonstrates that di-π-methane reactions can also take place via radical-cation intermediates. In some instances, imine and olefin centered cation-radical intermediates, generated by SET-sensitized irradiation, undergo alternative reactions to produce isoquinoline and benzoazepine products.
Photochemical reactivity of 1-substituted-1-aza-1,4-dienes promoted by electron-acceptor sensitizers. Di-π-methane rearrangements and alternative reactions via radical-cation intermediates
Armesto, Diego,Ortiz, Maria J.,Agarrabeitia, Antonia R.,Aparicio-Lara, Santiago,Martin-Fontecha, Mar,Liras, Marta,Martinez-Alcazar, M. Paz
, p. 9397 - 9405 (2007/10/03)
Irradiation of a series of β,γ-unsaturated imines, oxime acetates, and oxime methyl ethers, using 9,10-dicyanoanthrathene (DCA) or dicyanodurene (DCD) as electron acceptor sensitizers, affords the corresponding cyclopropanes resulting from 1-aza-di-π-methane rearrangements via radical cations. In some cases, alternative reactions of these intermediates occur to yield nitriles, dihydroquinolines, dihydronaphthalene derivatives, and cycloaddition products. Some of these products result from reactions via alkene radical-cation intermediates while others arise by pathways involving imine radical-cation intermediates. The yields of products formed in these processes were significantly higher when DCD was used as electron-acceptor sensitizer instead of DCA.
Photochemistry of the Carbon-Nitrogen Double Bond. Part 2. An Investigation of the 3-Methylenepropan-1-imine and 3-Oxopropan-1-imine Chromophores
Pratt, Albert C.,Abdul-Majid, Qais
, p. 359 - 364 (2007/10/02)
The synthesis of the non-conjugated imino compounds N-methoxy-2,2,4-trimethyl-1-phenylpent-3-en-1-imine (8), N-methoxy-2,2-dimethyl-4,4-diphenylbut-3-en-1-imine (9), 2-(1,1-dimethyl-3,3-diphenylprop-2-enyl)-4,4-dimethyl-4,5-dihydro-oxazole (10), and 2-ben
