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

Access to Document

10.1080/10426500701735452

Fingerprint Dive into the research topics of 'Ambident electrophilicity of 5-membered ring phosphate triesters'. Together they form a unique fingerprint.

Cite this

@article{410982c0a2764ed0906ae871ff2ebc75,

title = "Ambident electrophilicity of 5-membered ring phosphate triesters",

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.",

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

author = "Nissan Ashkenazi and Yoffi Segall and Yishai Karton and Zade, {Sanjio S.} and Michael Bendikov",

year = "2008",

month = feb,

day = "1",

doi = "10.1080/10426500701735452",

language = "English",

volume = "183",

pages = "420--424",

journal = "Phosphorus, Sulfur and Silicon and the Related Elements",

issn = "1042-6507",

publisher = "Taylor and Francis Ltd.",

number = "2-3",

}

TY - JOUR

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

UR - http://www.scopus.com/inward/record.url?scp=45849123912&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=45849123912&partnerID=8YFLogxK

U2 - 10.1080/10426500701735452

DO - 10.1080/10426500701735452

M3 - Article

AN - SCOPUS:45849123912

VL - 183

SP - 420

EP - 424

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 -