Journal of Organic Chemistry p. 1070 - 1073 (1989)
Update date:2022-08-29
Topics:
Hwu, Jih Ru
Wang, Naelong
Yung, Richard T.
The possibility of the Me3Si- species to be a nucleofuge of a compound containing the NSiMe3 group was investigated.Treatment of hydrazines with 1.1 equiv of Me3SiCl, Me3SiSiMe3, or Ph2MeSiSiMePh2 in the presence of 1.0 equiv of potassium hydride gave the corresponding 2-tetrazenes (R1R2NN=NNR1R2) in fair to good yields.The hydrazines included 1-methyl-1-phenylhydrazine (9), 1-aminopiperidine (10), 1-amino-2,6-dimethylpiperidine (11), 4-aminomorpholine (12), and 1-aminohomopiperidine (13).In these reactions, Me3SiCl, Me3SiSiMe3, and Ph2MeSiSiMePh2 acted as oxidizing agents.Results from control experiments supported the proposed mechanism: silylation of hydrazines gave monosilylhydrazines, decomposition of monosilylhydrazines generated aminonitrenes, and dimerization of aminonitrenes afforded 2-tetrazenes.In the decomposition of monosilylhydrazines, Me3Si- behaved as a leaving group from the NSiMe3 moiety.
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