Photochemical reactions of aromatic compounds. Part 34. Direct photocyanation of arenes with sodium cyanide in the presence of electron acceptors

Abstract

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.