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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Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 75th anniversary
Original Russian Text © E.A. Popova, Yu.N. Pavlyukova, E.V. Popov, V.A. Ostrovskii, R.E. Trifonov, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 6, pp. 902–906.
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Popova, E.A., Pavlyukova, Y.N., Popov, E.V. et al. Kinetics of azidation of isomeric benzenedicarbonitriles. Russ J Org Chem 45, 890–894 (2009). https://doi.org/10.1134/S1070428009060153
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DOI: https://doi.org/10.1134/S1070428009060153