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5-phenyl-2H-tetrazol-2-ylmethyl ketones in the synthesis of tetrazolylalkanols and tetrazolyl(hydroxy)alkylphosphonates

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Abstract

The reduction of 1-(5-phenyl-2H-tetrazol-2-yl)propan-2-one and 1-phenyl-2-(5-phenyl-2H-tetrazol-2-yl)ethanone with sodium tetrahydridoborate gave 1-(5-phenyl-2H-tetrazol-2-yl)propan-1-ol and 1-phenyl-2-(5-phenyl-2H-tetrazol-2-yl)ethanol, respectively. Only 1-(5-phenyl-2H-tetrazol-2-yl)propan-2-one was reduced with baker’s yeast with an appreciable yield. 1-(5-Phenyl-2H-tetrazol-2-yl)propan-2-one and 1-phenyl-2-(5-phenyl-2H-tetrazol-2-yl)ethanone reacted with diethyl phosphonate in the presence of potassium fluoride to produce the corresponding diethyl [hydroxy(5-phenyl-2H-tetrazol-2-yl)alkyl]phosphonates.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    A. S. Krylov, A. V. Dogadina & R. E. Trifonov

  2. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    R. E. Trifonov

Authors
  1. A. S. Krylov
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  2. A. V. Dogadina
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  3. R. E. Trifonov
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Correspondence to R. E. Trifonov.

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Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 80th anniversary

Original Russian Text © A.S. Krylov, A.V. Dogadina, R.E. Trifonov, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 6, pp. 907–909.

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Krylov, A.S., Dogadina, A.V. & Trifonov, R.E. 5-phenyl-2H-tetrazol-2-ylmethyl ketones in the synthesis of tetrazolylalkanols and tetrazolyl(hydroxy)alkylphosphonates. Russ J Org Chem 50, 892–894 (2014). https://doi.org/10.1134/S1070428014060219

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  • DOI: https://doi.org/10.1134/S1070428014060219

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