Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity

Peter R. Ashton; Patrizia Calcagno; Neil Spencer; Kenneth D.M. Harris; Douglas Philp

doi:10.1021/ol005604m

Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity

Peter R. Ashton, Patrizia Calcagno, Neil Spencer, Kenneth D.M. Harris^*, Douglas Philp

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

Abstract

(Matrix Presented) The rational design of a bis(phosphine oxide) host which is capable of binding a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationalized in terms of the enhancement of the nucleophilicity of the benzylic amine.

Original language	English (US)
Pages (from-to)	1365-1368
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	10
DOIs	https://doi.org/10.1021/ol005604m
State	Published - May 18 2000

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol005604m

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title = "Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity",

abstract = "(Matrix Presented) The rational design of a bis(phosphine oxide) host which is capable of binding a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationalized in terms of the enhancement of the nucleophilicity of the benzylic amine.",

author = "Ashton, {Peter R.} and Patrizia Calcagno and Neil Spencer and Harris, {Kenneth D.M.} and Douglas Philp",

year = "2000",

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T1 - Using polarization effects to alter chemical reactivity

T2 - A simple host which enhances amine nucleophilicity

AU - Ashton, Peter R.

AU - Calcagno, Patrizia

AU - Spencer, Neil

AU - Harris, Kenneth D.M.

AU - Philp, Douglas

PY - 2000/5/18

Y1 - 2000/5/18

N2 - (Matrix Presented) The rational design of a bis(phosphine oxide) host which is capable of binding a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationalized in terms of the enhancement of the nucleophilicity of the benzylic amine.

AB - (Matrix Presented) The rational design of a bis(phosphine oxide) host which is capable of binding a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationalized in terms of the enhancement of the nucleophilicity of the benzylic amine.

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Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity

Abstract

ASJC Scopus subject areas

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