Synthesis 2012; 44(18): 2938-2946
DOI: 10.1055/s-0032-1316764
paper
© Georg Thieme Verlag Stuttgart · New York

Atom-Economic, Metal- and Halogen-Free Synthesis of Podands: α,ω-Diphosphines and Their Chalcogenides Separated by Alkane Diol Spacers

Authors

  • Ludmila A. Oparina

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation , Fax: +7(3952)419346    Email: boris_trofimov@irioch.irk.ru
  • Nina K. Gusarova

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation , Fax: +7(3952)419346    Email: boris_trofimov@irioch.irk.ru
  • Oksana V. Vysotskaya

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation , Fax: +7(3952)419346    Email: boris_trofimov@irioch.irk.ru
  • Nikita A. Kolyvanov

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation , Fax: +7(3952)419346    Email: boris_trofimov@irioch.irk.ru
  • Alexander V. Artem’ev

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation , Fax: +7(3952)419346    Email: boris_trofimov@irioch.irk.ru
  • Boris A. Trofimov*

    A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation , Fax: +7(3952)419346    Email: boris_trofimov@irioch.irk.ru
Further Information

Publication History

Received: 05 June 2012

Accepted after revision: 08 July 2012

Publication Date:
08 August 2012 (online)


Graphical Abstract

Abstract

Secondary phosphines and phosphine chalcogenides add to the divinyl ether of α,ω-alkane diols regio- and chemoselectively under free-radical conditions (UV irradiation or AIBN, 2:1 reactants molar ratio) to give anti-Markovnikov diadducts in good to excellent yields (65–98%).