A convenient s rn 1 synthesis of aromatic nitriles from diazonium salts via diazosulfides

G Petrillo, M Novi, G Garbarino, C Dell'erba

Index: Petrillo, Giovanni; Novi, Marino; Garbarino, Giacomo; Dell'erba, Carlo Tetrahedron, 1987 , vol. 43, # 20 p. 4625 - 4634

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Citation Number: 31

Abstract

Properly substituted diazosulfides XC6H4-N= N-SPh (1)(either isolated or generated in situ from arenediazonium tetrafluoroborates and sodium benzenethiolate) react with tetrabutylammonium cyanide, in Me2SO under photon or electron stimulation, leading to nitriles XC6H4CN (2). Satisfactory yields of 2, comparable with those of the Sandmeyer reaction, are obtained when X= 3-or 4-CF3, 2-, 3-, or 4-CN, 4-F, 4-MeO, 3-MeCO, 4-NO2, ...