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

doi:10.1055/s-2007-983847

PAPER

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;

Abstract

All articles of this category

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.

Key words

aliphatic nitro compounds - poly(β-hydroxyiminoalkyl)amines - N,N-bis(siloxy)enamines - tripod ligands

Full Text

References

<A NAME="RP03907SS-1A">1a</A> Edison SE. Hotz RP. Baldwin MJ. Chem. Commun. (Cambridge) 2004, 1212

<A NAME="RP03907SS-1B">1b</A> Goldcamp MJ. Robison SE. Krause Bauer JA. Baldwin MJ. Inorg. Chem. 2002, 41: 2307

<A NAME="RP03907SS-2A">2a</A> Matthaiopoulos G. Ber. Dtsch. Chem. Ges. 1898, 31: 2396

<A NAME="RP03907SS-2B">2b</A> Korten H. Scholl R. Ber. Dtsch. Chem. Ges. 1901, 34: 1904

<A NAME="RP03907SS-2C">2c</A> Ogloblin KA. Potekhin AA. J. Org. Chem. USSR (Engl. Transl.) 1965, 399

<A NAME="RP03907SS-3">3</A> Goldcamp MJ. Rosa DT. Landers NA. Mandel SM. Krause Bauer JA. Baldwin MJ. Synthesis 2000, 2033

<A NAME="RP03907SS-4A">4a</A> Dilman AD. Tishkov AA. Lyapkalo IM. Ioffe SL. Strelenko YuA. Tartakosky VA. Synthesis 1998, 181

<A NAME="RP03907SS-4B">4b</A> Dilman AD. Tishkov AA. Lyapkalo IM. Ioffe SL. Kachala VV. Strelenko YuA. Tartakosky VA. J. Chem. Soc., Perkin Trans. 1 2000, 2926

<A NAME="RP03907SS-4C">4c</A> Sukhorukov AYu. Bliznets IV. Lesiv AV. Khomutova YuA. Strelenko YuA. Ioffe SL. Synthesis 2005, 1077

<A NAME="RP03907SS-5A">5a</A> Makarenkova LM. Bliznets IV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Russ. Chem. Bull. 2000, 49: 1261

<A NAME="RP03907SS-5B">5b</A> Feger H. Simchen G. Liebigs Ann. Chem. 1986, 1456

<A NAME="RP03907SS-6">6</A> Lesiv AV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Helv. Chim. Acta 2002, 85: 3489

<A NAME="RP03907SS-7">7</A> Lesiv AV. Ioffe SL. Strelenko YuA. Tartakovsky VA. Bliznets IV. Tartakovsky VA. Mendeleev Commun. 2002, 99

<A NAME="RP03907SS-8">8</A>An analogue of B, where both chlorine atoms are replaced with NO₃ groups, is described.^1b

<A NAME="RP03907SS-9A">9a</A> Goldcamp MJ. Krause Bauer JA. Baldwin MJ. J. Chem. Crystallogr. 2005, 35: 77

<A NAME="RP03907SS-9B">9b</A> Rosa DT. Krause Bauer JA. Baldwin MJ. Inorg. Chem. 2001, 40: 1606

<A NAME="RP03907SS-9C">9c</A> Goldcamp MJ. Edison SE. Squires LN. Rosa DT. Vowels NK. Coker NL. Krause Bauer JA. Baldwin MJ. Inorg. Chem. 2003, 42: 717

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.

<A NAME="RP03907SS-11">11</A> 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