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

Nóra Zsuzsa Kiss, Anna Kaszás, L. Drahos, Zoltán Mucsi, G. Keglevich

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

Diethyl α-hydroxy-benzylphosphonate undergoes nucleophilic substitution with primary amines of sufficient reactivity at around 100 °C to afford the corresponding α-aminophosphonates. The substitution can be enhanced by microwave irradiation. The reaction takes place with surprising ease due to the neighbouring group effect of the PO moiety as was justified by DFT calculations carried out to evaluate the mechanism of the substitution under discussion.

Original languageEnglish
Pages (from-to)207-209
Number of pages3
JournalTetrahedron Letters
Volume53
Issue number2
DOIs
Publication statusPublished - Jan 11 2012

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Microwaves
Amines
Substitution reactions
Carbon
Atoms
Microwave irradiation
Discrete Fourier transforms

Keywords

  • α-Aminophosphonate
  • α-Hydroxyphosphonate
  • Microwave
  • Neighbouring group effect
  • Nucleophilic substitution

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A neighbouring group effect leading to enhanced nucleophilic substitution of amines at the hindered α-carbon atom of an α-hydroxyphosphonate. / Zsuzsa Kiss, Nóra; Kaszás, Anna; Drahos, L.; Mucsi, Zoltán; Keglevich, G.

In: Tetrahedron Letters, Vol. 53, No. 2, 11.01.2012, p. 207-209.

Research output: Contribution to journalArticle

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