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Tetrasubstituted Tetrazenes (Me3E)2N-N=N-N(EMe3)2 (E = Si, Ge, Sn): Reactivity
Wiberg, Nils,Bayer, Heiner,Vasisht, Sham Kumar,Meyers, Rene
, p. 2916 - 2927 (2007/10/02)
By substitution of the silyl, germyl, or stannyl groups, (Me3Si)2N-N=N-N(SiMe3)2 (1) reacts with variable amounts of trifluoroacetic acid to form (Me3Si)4-nN4Hn, (Me3Ge)2N-N=N-N(GeMe)2 (2) with variable amounts of methanol to form (Me3Ge)4-nN4Hn, and (Me3Sn)2N-N=N-N(SnMe3)2 (3) with variable amounts of trimethylchlorosilane to give (Me3Sn)4-nN4(SiMe3)n (n = 1-4).The reaction of 1 with benzenesulfonyl isocyanate leads by substitution and cyclization to silylated 5-hydroxytetrazole 12.Substitution in connection with thermolysis of the substitution products formed is found in the reaction of 1 with methanol, aluminium chloride, or nitrosyl chloride and in the reaction of 3 with trimethylstannane, acetone, or nitrosobenzene.By oxidation of 1 with chlorine, bromine, or p-benzoquinone and of 3 with p-benzoquinone or oxygen, all tetrazene nitrogen is envolved.The reduction of 1 with hydrogen or alkali metals leads to nitrogen and (Me3Si)2NH or (Me3Si)2NM.
