56666-55-8Relevant articles and documents
Decarboxylative photosubstitution of dicyanobenzenes with aliphatic carboxylate ions
Itou, Tatsuya,Yoshimi, Yasuharu,Morita, Toshio,Tokunaga, Yuji,Hatanaka, Minoru
experimental part, p. 263 - 269 (2009/04/07)
The photoreaction of dicyanobenzenes with aliphatic carboxylate ions afforded alkylcyanobenzenes and alkyldicyanobenzenes via decarboxylative substitution. The redox-photosensitized reaction system was effective in improving the product yield. The efficie
PHOTOCHEMICAL REACTIONS OF ARENECARBONITRILES WITH ALIPHATIC AMINES. 2. EFFECT OF AMINE STRUCTURE ON AMINYL VS. alpha -AMINOALKYL RADICAL FORMATION.
Lewis,Correa
, p. 194 - 198 (2007/10/02)
The photochemical reactions of 9-phenanthrenecarbonitrile with several secondary and primary amines and triethylamine have been investigated. Rate constants for fluorescence quenching by secondary and primary amines decrease with amine alpha -alkylation in spite of increased electron-donor ability of the more substituted amines. This trend is attributed to a steric effect on the equilibrium constant for reversible exciplex formation. The reactions of secondary and primary amines in nonpolar solvent result in selective N-H vs. alpha C-H transfer from amine to arene, via a singlet exciplex. The ratio of alpha -C-H/N-H transfer increases with alpha -alkylation and increased solvent polarity and is larger for secondary vs. primary amines.
Photochemical Reactions of Aromatic Compounds. Part 34. Direct Photocyanation of Arenes with Sodium Cyanide in the Presence of Electron Acceptors
Yasuda, Masahide,Pac, Chyondgjin,Sakurai, Hiroshi
, p. 746 - 750 (2007/10/02)
Efficient photocyanation of various arenes with sodium cyanide in 9:1 acetonitrile-water occurs in the presence of such electron acceptors as p-dicyanobenzene, 1-cyanonaphthalene, or 9-cyanophenanthrene.Under nitrogen, photocyanation of phenanthrene, anthracene, naphthalene, and 2,3-dimethylnaphthalene gives both the corresponding hydrocyanation products and the aromatic nitriles, while complex mixtures are formed with other arenes.Under oxygen, a variety of arenes which are electron donors in nature can be efficiently cyanated upon irradiation to give the aromatic nitriles.Cyanation of naphthalene derivatives gives only 1-cyanonaphthalene compounds whereas phenanthrene and anthracene are cyanated at C-9.