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

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
› Author Affiliations
Further Information

Publication History

Received: 05 June 2012

Accepted after revision: 08 July 2012

Publication Date:
08 August 2012 (online)


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%).