Limits to oxidation of organic substrates. SET oxidative processes of commonly used solvents as revealed through the photochemical reaction with 1,2,4,5- benzenetetracarbonitrile
作者： Maurizio Fagnoni , Matteo Vanossi , Mariella Mella , Angelo Albini
DOI: 10.1016/0040-4020(95)01013-0
关键词:
摘要: Abstract The chemical reactivity upon single electron transfer of some common solvents has been explored. This obtained by using photo excited benzene-1,2,4,5-tetracarbonitrile (TCB) as the oxidant. Under this condition acetonitrile, isobutyronitrile, methanol and trifluoroethanol all undergo α-deprotonation from their radical cations giving alkyl radicals which are trapped TCB − . yield aikylbenzenetricarbonitriles or products derived them. reaction two aliphatic nitriles, occurs only in presence protic additives, is accompanied a different fragmentation leading to methyl (or respectively isopropyl) radicals. Trifluoroacetic acid decarboxylates, probably via oxidation anion. irradiation neat (rather than MeOH-MeCN mixtures) leads addition onto cyano group. finally dicyanoindoles.
elsevier.com
sci-hub.se 参考文章(23)
Przemyslaw Maslak, Fragmentations by photoinduced electron transfer. Fundamentals and practical aspects Topics in Current Chemistry. ,vol. 168, pp. 1- 46 ,(1993) , 10.1007/3-540-56746-1_7
Angelo Albini, Elisa Fasani, Mariella Mella, PET-reactions of aromatic compounds Topics in Current Chemistry. ,vol. 168, pp. 143- 173 ,(1993) , 10.1007/3-540-56746-1_10
Organic Syntheses by Oxidation with Metal Compounds Springer US. ,(1986) , 10.1007/978-1-4613-2109-5
Saul Patai, The Chemistry of amidines and imidates UMI Books on Demand. ,(1975)
M. F. Haley, K. Yates, Photochemistry of carbon-nitrogen multiple bonds in aqueous solution. 1. Aromatic oximes, oxime ethers, and nitriles Journal of Organic Chemistry. ,vol. 52, pp. 1817- 1824 ,(1987) , 10.1021/JO00385A030
Elisa Fasani, Diego Peverali, Angelo Albini, Alkyl radicals from t-butyl esters through photoinduced electron transfer Tetrahedron Letters. ,vol. 35, pp. 9275- 9278 ,(1994) , 10.1016/0040-4039(94)88486-2
Matthew A. Kellett, David G. Whitten, Ian R. Gould, William R. Bergmark, Surprising differences in the reactivity of cyanoaromatic radical anions generated by photoinduced electron transfer Journal of the American Chemical Society. ,vol. 113, pp. 358- 359 ,(1991) , 10.1021/JA00001A052
Mauro Freccero, Mariella Mella, Angelo Albini, The photochemical reactions of 9,10-anthracenedicarbonitrile and 1,4-naphthalenedicarbonitrile in acetonitrile in the presence of bases Tetrahedron. ,vol. 50, pp. 2115- 2130 ,(1994) , 10.1016/S0040-4020(01)85074-2
Angelo Albini, Mariella Mella, Mauro Freccero, A new method in radical chemistry: Generation of radicals by photo-induced electron transfer and fragmentation of the radical cation Tetrahedron. ,vol. 50, pp. 575- 607 ,(1994) , 10.1016/S0040-4020(01)80780-8
Marye Anne Fox, PHOTOINDUCED ELECTRON TRANSFER Photochemistry and Photobiology. ,vol. 52, pp. 617- 627 ,(1990) , 10.1111/J.1751-1097.1990.TB01808.X