Download PDF
Synthesis 2006(24): 4159-4162  
DOI: 10.1055/s-2006-950340
PAPER
© Georg Thieme Verlag Stuttgart · New York

Non-Catalyzed, Atom-Economic, High-Yield Synthesis of Tertiary α-Hydroxyphosphane Selenides

Nina K. Gusarova, Nina I. Ivanova, Nataliya A. Konovalova, Boris G. Sukhov, Ludmila V. Baikalova, Lidiya M. Sinegovskaya, Dmitriy V. Pavlov, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: gusarova@irioch.irk.ru;
Further Information

Publication History

Received 12 July 2006
Publication Date:
02 November 2006 (online)

   Permissions and Reprints All articles of this category

Abstract

First examples of a facile hydroselenophosphorylation of aldehydes are reported. Nucleophilic addition of P,Se-ambident secondary phosphane selenides to a series of aldehydes proceeds under catalyst-free conditions at room temperature to give tertiary α-hydroxyphosphane selenides in high yield.

Key words

hydroselenophosphorylation - α-hydroxyphosphane selenides - aldehydes - nucleophilic addition

    References

  • 1a Belletti D. Graiff C. Massera C. Pattacini R. Predieri G. Tiripicchio A. Inorg. Chim. Acta  2003,  356:  187 
    Search in Google Scholar
  • 1b Adams RD. Kwon OS. Sanyal S. Organomet. Chem.  2003,  681:  258 
    Search in Google Scholar
  • 1c Hussain MS. Isab AA. Chemical Crystallogr.  2000,  30:  731 
    Search in Google Scholar
  • 1d Malik S. Duddeck H. Omelanczuk J. Choudhary M. Chirality  2002,  14:  407 
    Search in Google Scholar
  • 1e Cauzzi D. Graiff C. Massera C. Predieri G. Tiripicchio A. Inorg. Chim. Acta  2000,  300-302:  471 
    Search in Google Scholar
  • 1f Belletti D. Graiff C. Massera C. Pattacini R. Predieri G. Tiripicchio A. Inorg. Chim. Acta.  2003,  350:  421 
    Search in Google Scholar
  • 1g Steinberger HU. Ziemer B. Meisel M. Acta Crystallogr.  2001,  C57:  323 
    Search in Google Scholar
  • 1h Kimura T. Murai T. Chem. Lett.  2004,  33:  879 
    Search in Google Scholar
  • 2a Purdela D. Vilceanu R. Chemistry of Organic Compounds of Phosphorus (in Russian)   Nauka; Moscow: 1972. 
    Crossref
  • 2b Hoge B. Neufeind S. Hettel S. Wiebe W. Thösen C. J. Organomet. Chem.  2005,  690:  2382 
    CrossrefSearch in Google Scholar
  • 2c Ivanova NI. Gusarova NK. Konovalova NA. Sinegovskaya LM. Samoylov VG. Markosyan SM. Avseenko ND. Sukhov BG. Trofimov BA. Russ. J. Gen. Chem. (Engl. Transl.)  2006,  76:  98 
    CrossrefSearch in Google Scholar
  • 2d Ivanova NI. Gusarova NK. Nikitina EA. Albanov AI. Sinegovskaya LM. Nikitin MV. Konovalova NA. Trofimov BA. Phosphorus, Sulfur Silicon Relat. Elem.  2004,  179:  7 
    CrossrefSearch in Google Scholar
  • 2e Gusarova NK. Reutskaya AM. Ivanova NI. Medvedeva AS. Demina MM. Novopashin PS. Afonin AV. Albanov AI. Trofimov BA. J. Organomet. Chem.  2002,  659:  172 
    CrossrefSearch in Google Scholar
  • 2f Ivanova NI. Gusarova NK. Nikitina EA. Medvedeva SA. Al’pert ML. Trofimov BA. Chem. Heterocycl. Compd. (Engl. Transl.)  2004,  520 
    Crossref
  • 2g Gusarova NK. Arbuzova SN. Reutskaya AM. Ivanova NI. Baikalova LV. Sinegovskaya LM. Chipanina NN. Afonin AV. Ziryanova IA. Chem. Heterocycl. Compd. (Engl. Transl.)  2002,  71 
    Crossref
  • 2h Chipanina NN. Baikalova LV. Sinegovskaya LM. Kanitskaya LV. Fedorov SV. Zyryanova IA. Ivanova NI. Reutskaya AM. Tiunov MP. Gusarova NK. Trofimov BA. Russ. J. Gen. Chem. (Engl. Transl.)  2004,  74:  540 
    CrossrefSearch in Google Scholar
  • 2i Baikalova LV. Zyryanova IA. Chipanina NN. Sinegovskaya LM. Ivanova NI. Mamaseva TV. Gusarova NK. Afonin AV. Trofimov BA. Russ. J. Gen. Chem. (Engl. Transl.)  2005,  75:  200 
    CrossrefSearch in Google Scholar
  • 3a Well M. Schmutzler R. Phosphorus, Sulfur Silicon Relat. Elem.  1992,  72:  171 
    Search in Google Scholar
  • 3b Gusarova NK. Ivanova NI. Konovalova NA. Avseenko ND. Sukhov BG. Larina LI. Trofimov BA. In Proceedings of the 7th IUPAC International Conference on the Heteroatom Chemistry   Shanghai; China: 2004.  p.115 
  • 3c Trofimov BA. Gusarova NK. Ivanova NI. Konovalova NA. Bogdanova MV. Albanov AI. Avseenko ND. Sukhov BG. Russ. J. Gen. Chem. (Engl. Transl.)  2004,  74:  1625 
    Search in Google Scholar
  • 3d Ivanova NI. Baikalova LV. Konovalova NA. Ziryanova IA. Albanov AI. Sinegovskaya LM. Kukhareva VA. Tatarinova AA. Avseenko ND. Sukhov BG. Gusarova NK. Trofimov BA. Chem. Heterocycl. Compd. (Engl. Transl.)  2005,  365 
  • 3e Kosolapoff GM. Maier L. In Organic Phosphorus Compounds   Vol. 4:  Wiley-Interscience; New York: 1972. 
    Search in Google Scholar
  • 4 Sukhov BG. Gusarova NK. Ivanova NI. Bogdanova MV. Kagheva ON. Alexandrov GG. D’yachenko OA. Sinegovskaya LM. Malysheva SF. Trofimov BA. Zh. Strukt. Khim.  2005,  46:  1103 ; Chem. Abstr. 2006, 145, 907534
    Search in Google Scholar
  • 5a Trofimov BA. Brandsma L. Arbuzova SN. Malysheva SF. Gusarova NK. Tetrahedron Lett.  1994,  35:  7647 
    CrossrefSearch in Google Scholar
  • 5b Trofimov BA. Gusarova NK. Arbuzova SN. Russ. Chem. Rev.  1999,  68:  215 
    CrossrefSearch in Google Scholar