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Synthesis 1998; 1998(2): 181-185
DOI: 10.1055/s-1998-2019
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Novel Convenient Method for the Synthesis of N,N-Bis(trimethylsilyloxy)enamines

A. D. Dilman* , A. A. Tishkov, I. M. Lyapkalo, S. L. Ioffe, Yu. A. Strelenko, V. A. Tartakovsky
  • *N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation; Fax + 7(0 95)1 35 53 28; E-mail: lyapkalo@cacr.ioc.ac.ru
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Publication History

Publication Date:
31 December 2000 (online)

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Both primary and secondary aliphatic nitro compounds 1 were found to react with two equivalents of bromotrimethylsilane in the presence of triethylamine followed by aqueous workup to give appropriate N,N-bis(trimethylsilyloxy)enamines 3 in good isolated yields. Products 3, starting from some secondary and/or sterically hindered compounds 1, are synthesized from the corresponding silyl nitronates 2.

nitro compounds - bromotrimethylsilane - silylation - silyl nitronates - N,N-bis(trimethylsilyloxy)enamines