Issue 9, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of multifunctionalized phosphonic acidestersvia opening of oxiranes and azetidinium salts with phosphoryl-substituted carbanions

Agata Bakalarz-Jeziorna,a   Jan Helińskia  and  Bożena Krawiecka*a  

* Corresponding authors

a Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Łódź, Sienkiewicza, Poland

Abstract

Ring-opening of N,N-diethyl-3-benzyloxyazetidinium salt 1b and N,N-dibenzyl-2,3-epoxypropylamine 6 by phosphoryl-substituted carbanions generated from phosphonates 2a–e furnishes the multifunctional phosphonates 3a–e and 7a, 7b, 7e bearing the same carbon skeleton. The reaction of the heterocyclic electrophiles 1b and 6 with the P-allyl anion generated from 2f demonstrates the strong dependence of the α/γ-regioselectivity on the reaction conditions. Depending on the character of the electrophile and/or the reaction medium the regioselective synthesis of both α- and γ-regioisomers is realized.

Graphical abstract: Synthesis of multifunctionalized phosphonic acid esters via opening of oxiranes and azetidinium salts with phosphoryl-substituted carbanions

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Article information

DOI
https://doi.org/10.1039/B009720I
Article type
Paper
Submitted
04 Dec 2000
Accepted
20 Feb 2001
First published
21 Mar 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 1086-1090

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Synthesis of multifunctionalized phosphonic acid esters via opening of oxiranes and azetidinium salts with phosphoryl-substituted carbanions

A. Bakalarz-Jeziorna, J. Heliński and B. Krawiecka, J. Chem. Soc., Perkin Trans. 1, 2001, 1086 DOI: 10.1039/B009720I

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