78044-70-9Relevant academic research and scientific papers
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 (1981)
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.
Mechanisms for Aromatic Photocyanation: Naphthalene and Biphenyl
Bunce, Nigel J.,Bergsma, John P.,Schmidt, John L.
, p. 713 - 719 (2007/10/02)
Photocyanation of naphthalene and biphenyl has been studied in the systems ArH-KCN-aqueous CH3CN and ArH-NaCN-CH3OH.The reaction is first order in CN(-) and in ground state ArH as well as in excited ArH.The proposed mechanism involves the formation of a singlet excimer, which dissociates into radical ions before the attack of cyanide ion.Photocyanations in the presence of oxidants such as p-dicyanobenzene and persulphate ion proceed by oxidation of the singlet excited hydrocarbon to form a radical cation directly.
