Photochemicalcis-transIsomerization of 2,4,5-Triphenylimidazolines
作者： Teruo Matsuura , Yoshikatsu Ito
DOI: 10.1246/BCSJ.48.3669
关键词:
摘要: Irradiation of cis- (amarine; I) and trans- (isoamarine; II) 2,4,5-triphenylimidazolines in acetonitrile or benzene gave a photostationary mixture trans-isomers, the latter predominating over former. On irradiation dilute acetone solution under conditions that absorbed most incident light, cis-trans isomerization occurred only with isoamarine but not amarine. In acetone, 2,4,5-triphenylimidazole (III) was also formed. Two kinds intermediate species for were proposed; imidazolinyl radicals IV and/or V formed by hydrogen abstraction excited state (in acetone) biradical zwitterionic VIa cleavage from I II benzene). Evidences intermediacy are presented.
csj.jp参考文章(23)
A. G. Anastassiou, R. B. Hammer, Photochemical behavior of certain N-substituted diphenylaziridines. Question of isomerization vs. fragmentation Journal of the American Chemical Society. ,vol. 94, pp. 303- 305 ,(1972) , 10.1021/JA00756A067
J. A. Kerr, Bond Dissociation Energies by Kinetic Methods Chemical Reviews. ,vol. 66, pp. 465- 500 ,(1966) , 10.1021/CR60243A001
N. Gakis, M. Märky, H.-J. Hansen, H. Schmid, Zur Photodimerisierung von 3‐Phenyl‐2H‐azirinen. Vorläufige Mitteilung Helvetica Chimica Acta. ,vol. 55, pp. 748- 752 ,(1972) , 10.1002/HLCA.19720550303
Y. Ito, T. Matsuura, Photoinduced reactions—LXXX Tetrahedron. ,vol. 31, pp. 1373- 1380 ,(1975) , 10.1016/0040-4020(75)87066-9
Peter. Beak, John L. Miesel, The photorearrangement of 2,3-dihydropyrazines Journal of the American Chemical Society. ,vol. 89, pp. 2375- 2384 ,(1967) , 10.1021/JA00986A024
Saul G. Cohen, Chi Hua Wang, MERCAPTAN CATALYSIS IN THERMONEUTRAL FREE RADICAL EXCHANGE: R· + R*H [UNK] RH + R*· Journal of the American Chemical Society. ,vol. 77, pp. 4435- 4436 ,(1955) , 10.1021/JA01621A090
Harold H. Strain, BENZOIN-ANIL-ANILIDE AND BENZOIN-PARA-TOLYL PARA-TOLUIDE AS AMMONO BENZOIN ACETALS Journal of the American Chemical Society. ,vol. 51, pp. 269- 273 ,(1929) , 10.1021/JA01376A035
Naoki TOSHIMA, Hidefumi HIRAI, Shoji MAKISHIMA, Photoreduction of Diphenylmethylenimine The Journal of the Society of Chemical Industry, Japan. ,vol. 72, pp. 184- 187 ,(1969) , 10.1246/NIKKASHI1898.72.184
Peter John. Wagner, Solvent effects on type II photoelimination of phenyl ketones Journal of the American Chemical Society. ,vol. 89, pp. 5898- 5901 ,(1967) , 10.1021/JA00999A028
J. P. Ferris, F. R. Antonucci, Chemical evolution. XVII. Mechanisms of the photochemical rearrangements of ortho-substituted benzene derivatives and related heterocycles Journal of the American Chemical Society. ,vol. 96, pp. 2014- 2019 ,(1974) , 10.1021/JA00814A006