Kinetics of azidation of isomeric benzenedicarbonitriles |
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| Authors: | E A Popova Yu N Pavlyukova E V Popov V A Ostrovskii R E Trifonov |
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| Institution: | (1) St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia |
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| Abstract: | Rate constants and activation parameters of two-step azidation of isomeric dicyanobenzenes with dimethylammonium azide in DMF at 70–100°C were determined. Tetrazole rings are formed from cyano groups in dicyanobenzenes in a stepwise mode following the 1,3-dipolar cycloaddition pattern. The rate of azidation of isomeric dicyanobenzenes is considerably higher than the rate of subsequent azidation of intermediate cyanophenyltetrazolides. The azidation rate constant decrease in going from m-dicyanobenzene to its para and ortho isomers. |
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