Syntheses of Arylcyanotriazenes and Related Compounds

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概要

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• 1-Aryl-3-cyanotriazene potassium salts (IIa-j) were synthesized by treating the corresponding arylazides (Ia-j) with potassium cyanide. When IIa-j were treated with dimethyl sulfate in the presence of dicyclohexyl-18-crown ether-6 (18-crown-6), methylation occurred at N^1 and N^3 of the triazeno group. The resulting two isomers, 1-aryl-3-cyano-1-methyltriazenes (IIIa-j) and 1-aryl-3-cyano-3-methyltriazenes (IVa-f) were all separable by means of chromatography on silica gel. However, several of the 3-isomers (IVg-j) were not isolated. On the other hand, the direct alkylation of arylcyanotriazene potassium salts (IIa, c, e) with dimethyl sulfate in methanol gave only the 1-methyl derivatives, 1-aryl-3-cyano-1-methyltriazenes (IIIa, c, e). The alkylated positions in these products were determined by chemical and spectral studies. A clear correlation between the Hammett constants and the ^<13>C-nuclear magnetic resonance (^<13>C-NMR) chemical shifts of the nitrile carbons of (1-aryl-3-cyano) methyltriazenes (IIIa-j, IVa-f) was obtained.

• 公益社団法人日本薬学会の論文
• 1982-09-25

著者

• 神谷 庄造

  National Institute of Hygienic Sciences, University of Tokyo

• 丹野 雅幸

  National Institute of Hygienic Sciences

• 末吉 祥子

  National Institute of Hygienic Sciences

• 神谷 庄造

  National Institute Of Hygienic Sciences

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