Ambident electrophilicity of 5-membered ring phosphate triesters

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

doi:10.1080/10426500701735452

Ambident electrophilicity of 5-membered ring phosphate triesters

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

Weizmann Institute of Science, Israel

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	420-424
Number of pages	5
Journal	Phosphorus, Sulfur and Silicon and the Related Elements
Volume	183
Issue number	2-3
DOIs	https://doi.org/10.1080/10426500701735452
Publication status	Published - Feb 1 2008

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Keywords

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

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Inorganic Chemistry

Cite this

Ashkenazi, N., Segall, Y., Karton, Y., Zade, S. S., & Bendikov, M. (2008). Ambident electrophilicity of 5-membered ring phosphate triesters. Phosphorus, Sulfur and Silicon and the Related Elements, 183(2-3), 420-424. https://doi.org/10.1080/10426500701735452

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Access to Document

10.1080/10426500701735452