Synthesis 2007(18): 2862-2866  
DOI: 10.1055/s-2007-983847
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Convenient Method for the Synthesis of Poly(β-hydroxyiminoalkyl)amines from Aliphatic Nitro Compounds

Artem N. Semakin, Alexey Yu. Sukhorukov, Alexey V. Lesiv, Yulia A. Khomutova, Sema L. Ioffe*, Konstantin A. Lyssenko
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation
Fax: +7(495)1355328; e-Mail: iof@ioc.ac.ru;
Further Information

Publication History

Received 2 April 2007
Publication Date:
08 August 2007 (online)

Abstract

A general and efficient method for the synthesis of different poly(β-hydroxyiminoalkyl)amines from aliphatic nitro compounds and amines via terminal N,N-bis(siloxy)enamine intermediates is described.

    References

  • 1a Edison SE. Hotz RP. Baldwin MJ. Chem. Commun. (Cambridge)  2004,  1212 
  • 1b Goldcamp MJ. Robison SE. Krause Bauer JA. Baldwin MJ. Inorg. Chem.  2002,  41:  2307 
  • 2a Matthaiopoulos G. Ber. Dtsch. Chem. Ges.  1898,  31:  2396 
  • 2b Korten H. Scholl R. Ber. Dtsch. Chem. Ges.  1901,  34:  1904 
  • 2c Ogloblin KA. Potekhin AA. J. Org. Chem. USSR (Engl. Transl.)  1965,  399 
  • 3 Goldcamp MJ. Rosa DT. Landers NA. Mandel SM. Krause Bauer JA. Baldwin MJ. Synthesis  2000,  2033 
  • 4a Dilman AD. Tishkov AA. Lyapkalo IM. Ioffe SL. Strelenko YuA. Tartakosky VA. Synthesis  1998,  181 
  • 4b Dilman AD. Tishkov AA. Lyapkalo IM. Ioffe SL. Kachala VV. Strelenko YuA. Tartakosky VA. J. Chem. Soc., Perkin Trans. 1  2000,  2926 
  • 4c Sukhorukov AYu. Bliznets IV. Lesiv AV. Khomutova YuA. Strelenko YuA. Ioffe SL. Synthesis  2005,  1077 
  • 5a Makarenkova LM. Bliznets IV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Russ. Chem. Bull.  2000,  49:  1261 
  • 5b Feger H. Simchen G. Liebigs Ann. Chem.  1986,  1456 
  • 6 Lesiv AV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Helv. Chim. Acta  2002,  85:  3489 
  • 7 Lesiv AV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Bliznets IV. Tartakovsky VA. Mendeleev Commun.  2002,  99 
  • 8An analogue of B, where both chlorine atoms are replaced with NO3 groups, is described.1b
  • 8
  • 9a Goldcamp MJ. Krause Bauer JA. Baldwin MJ. J. Chem. Crystallogr.  2005,  35:  77 
  • 9b Rosa DT. Krause Bauer JA. Baldwin MJ. Inorg. Chem.  2001,  40:  1606 
  • 9c Goldcamp MJ. Edison SE. Squires LN. Rosa DT. Vowels NK. Coker NL. Krause Bauer JA. Baldwin MJ. Inorg. Chem.  2003,  42:  717 
  • 11 For clathrochelates based on oxime ligands, see: Voloshin YZ. Varzatskii OA. Kron TE. Belsky VK. Zavodnik VE. Strizhakova NG. Palchik AV. Inorg. Chem.  2000,  39:  1907 ; and references cited therein
10

CCDC 641328 and 641329 contain the supplementary crystallographic data for 6 and 7, respectively. These data can be obtained free of charge via http://www.ccdc.cam.ac.uk, by e-mailing or faxing a request to deposit@ccdc.cam.ac.uk or +44(1223)336033, respectively, or by writing to the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.