Ambident electrophilicity of 5-membered ring phosphate triesters

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

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


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
Issue number2-3
Publication statusPublished - Feb 1 2008


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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

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