Journal of the Chemical Society. Perkin transactions I p. 746 - 750 (1981)
Update date:2022-08-03
Topics:
Yasuda, Masahide
Pac, Chyondgjin
Sakurai, Hiroshi
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.
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