Ambident electrophilicity of 5-membered ring phosphate triesters

Nissan Ashkenazi, Yoffi Segall, Yishai Karton, Sanjio S. Zade, Michael Bendikov

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The reactions of 2-alkoxy-1,3,2-dioxaphospholane 2-oxide with various nucleophiles were studied both experimentally and theoretically. These studies show that 5-membered ring phosphate triesters act as ambident electrophiles: hard and bulky nucleophiles attack at the phosphorus while soft nucleophiles attack at the ring carbon.

Original languageEnglish
Pages (from-to)420-424
Number of pages5
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume183
Issue number2-3
DOIs
Publication statusPublished - Feb 2008

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Nucleophiles
Phosphorus
Oxides
Carbon
Phosphates
alkoxyl radical

Keywords

  • 2-Alkoxy-1,3,2-dioxaphospholane 2-oxide
  • Electrophilicity
  • Hard and soft nucleophiles
  • Steric bulk

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Ambident electrophilicity of 5-membered ring phosphate triesters. / Ashkenazi, Nissan; Segall, Yoffi; Karton, Yishai; Zade, Sanjio S.; Bendikov, Michael.

In: Phosphorus, Sulfur and Silicon and the Related Elements, Vol. 183, No. 2-3, 02.2008, p. 420-424.

Research output: Contribution to journalArticle

Ashkenazi, Nissan ; Segall, Yoffi ; Karton, Yishai ; Zade, Sanjio S. ; Bendikov, Michael. / Ambident electrophilicity of 5-membered ring phosphate triesters. In: Phosphorus, Sulfur and Silicon and the Related Elements. 2008 ; Vol. 183, No. 2-3. pp. 420-424.
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