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 › peer-review

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

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

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T1 - Ambident electrophilicity of 5-membered ring phosphate triesters

AU - Ashkenazi, Nissan

AU - Segall, Yoffi

AU - Karton, Yishai

AU - Zade, Sanjio S.

AU - Bendikov, Michael

PY - 2008/2/1

Y1 - 2008/2/1

N2 - 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.

AB - 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.

KW - 2-Alkoxy-1,3,2-dioxaphospholane 2-oxide

KW - Electrophilicity

KW - Hard and soft nucleophiles

KW - Steric bulk

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JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

SN - 1042-6507

IS - 2-3

ER -

Ambident electrophilicity of 5-membered ring phosphate triesters

Abstract

Keywords

ASJC Scopus subject areas

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