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Silylated Tetrazoles and Triazoles
Author(s) -
Gronde Ingo,
Mitzel Norbert W.
Publication year - 2009
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200900128
Subject(s) - tetrazole , chemistry , trimethylsilyl , triethylamine , trimethylsilyl azide , dimethylsilane , triazole , nuclear magnetic resonance spectroscopy , acetonitrile , medicinal chemistry , organic chemistry , azide
1‐Dimethysilyltetrazole ( 1 ) has been prepared from 1H‐tetrazole and chlorodimethylsilane in the presence of 2,6‐lutidine, bis(1‐tetrazolyl)dimethylsilane ( 2 ) from the reaction of 1H‐tetrazole, dimethyldichlorosilane and triethylamine and 5‐(trimethylsilylamino)‐1H‐tetrazole ( 3 ) from 5‐amino‐tetrazole monohydrate and hexamethyldisilazane. The reactions of 4‐amino‐1H‐1,2,4‐triazole with different amounts of hexamethyldisilazane gave rearrangement reactions yielding 1‐trimethylsilyl‐3‐(trimethylsilyl)amino‐1,2,4‐triazole ( 4 ) and 1‐trimethylsilyl‐3‐bis(trimethylsilyl)amino‐1,2,4‐triazole ( 5 ). The compounds were characterised by NMR spectroscopy ( 1 H, 13 C{ 1 H} and 29 Si NMR), by IR spectroscopy, mass spectrometry, elemental analyses and in the case of 3 , 4 and 5 by determination of their crystal structures by X‐ray diffraction. The structure of a cocrystallisate of 4‐amino‐1H‐1,2,4‐triazole with acetonitrile was also determined. Common structural distortions of silylated ring nitrogen atoms are discussed as well as hydrogen bonding motifs in the crystal structures.