A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered I+/--carbon atom of an I+/--hydroxyphosphonate

Diethyl alpha -hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 degree C to afford the corresponding alpha -aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising e...

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Bibliographic Details
Published in:Tetrahedron letters 2012-01, Vol.53 (2), p.207-209
Main Authors: Kiss, Nora Zsuzsa, Kaszas, Anna, Drahos, Laszlo, Mucsi, Zoltan, Keglevich, Gyorgy
Format: Article
Language:English
Subjects:
Amines
Irradiation
Mathematical analysis
Microwaves
Neighbouring
Nuclei
Tetrahedrons
Online Access:Get full text
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Summary:Diethyl alpha -hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 degree C to afford the corresponding alpha -aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising ease due to the neighbouring group effect of the P[inline image]O moiety as was justified by DFT calculations carried out to evaluate the mechanism of the substitution under discussion.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.11.026