Endo- and exocyclic N-alkylation of 1- and 5-aminotetrazoles with t-BuOH-HClO4: synthesis of mono-, di-, and tri-tert-butyl substituted aminotetrazolium salts |
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Authors: | Sergei V Voitekhovich Pavel N Gaponik Alexander S Lyakhov Oleg A Ivashkevich |
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Institution: | Research Institute for Physical Chemical Problems, Belarusian State University, 14 Leningradskaya Street, Minsk 220030, Belarus |
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Abstract: | A new method for the synthesis of 1,3,5-trisubstituted aminotetrazolium salts based on alkylation of 1- and 5-aminotetrazoles with the t-BuOH-HClO4 system is presented. Depending on the structure of the tetrazole substrate and reaction conditions, alkylation proceeds at the endocyclic nitrogen atoms as well as at the 1- and 5-amino groups giving mono-, di-, and tri-tert-butyl substituted tetrazolium salts. An X-ray diffraction investigation of 3-tert-butyl-1,5-bis(tert-butylamino)tetrazolium perchlorate and 5-amino-1,3-di-tert-butyltetrazolium chloride was carried out. |
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Keywords: | Aminotetrazoles Tetrazolium salts tert-Butylation Quaternization |
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