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Synthesis of 1,4‐phenylene‐ bis ‐aminomethanephosphonates: The stereochemical aspect

Synthesis of 1,4‐phenylene‐ bis ‐aminomethanephosphonates: The stereochemical aspect The synthesis of new 1,4‐phenylene‐bis‐(N‐alkylaminomethane)‐bis‐phosphonates 3Aa–3Da by the addition of dialkyl or diaryl phosphites to the azomethine bond of 1,4‐phenylene Schiff bases is reported. Some NMR studies on the stereochemistry of dialkyl phosphite addition to terephthalic bis‐imines showing the exclusive formation of the meso‐form are presented. The mechanism and the origin of such a high stereoselectivity are discussed. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:144–151, 2000 http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Heteroatom Chemistry Wiley

Synthesis of 1,4‐phenylene‐ bis ‐aminomethanephosphonates: The stereochemical aspect

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References (18)

Publisher
Wiley
Copyright
Copyright © 2000 John Wiley & Sons, Inc.
ISSN
1042-7163
eISSN
1098-1071
DOI
10.1002/(SICI)1098-1071(2000)11:2<144::AID-HC10>3.0.CO;2-Z
Publisher site
See Article on Publisher Site

Abstract

The synthesis of new 1,4‐phenylene‐bis‐(N‐alkylaminomethane)‐bis‐phosphonates 3Aa–3Da by the addition of dialkyl or diaryl phosphites to the azomethine bond of 1,4‐phenylene Schiff bases is reported. Some NMR studies on the stereochemistry of dialkyl phosphite addition to terephthalic bis‐imines showing the exclusive formation of the meso‐form are presented. The mechanism and the origin of such a high stereoselectivity are discussed. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:144–151, 2000

Journal

Heteroatom ChemistryWiley

Published: Jan 1, 2000

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