Synthesis of new dialkylaminopyridine acylation catalysts and their attachment to insoluble polymer supports

André Deratani; Graham D. Darling; Jean M.J. Fréchet

doi:10.1016/0032-3861(87)90235-7

Synthesis of new dialkylaminopyridine acylation catalysts and their attachment to insoluble polymer supports

André Deratani, Graham D. Darling, Jean M.J. Fréchet^*

^*Corresponding author for this work

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

28 Scopus citations

Abstract

Dialkylaminopyridines whose N-substituents bear a hydroxyl or amino group can be made economically from 4-cyanopyridine. Simple but selective alkylation of these compounds with commercial (chloromethyl) or (3-bromopropyl) polystyrene gives several new solid-phase catalysts which are highly active in promoting the acylation of hindered alcohols. Comparison of syntheses and reactivities, among these and some other heterocyclic polymers, illustrates several useful general principles of reactive polymer chemistry such as local concentration and microenvironment effects.

Original language	English (US)
Pages (from-to)	825-830
Number of pages	6
Journal	Polymer
Volume	28
Issue number	5
DOIs	https://doi.org/10.1016/0032-3861(87)90235-7
State	Published - Apr 1987
Externally published	Yes

Bibliographical note

Funding Information:
Financial support of this research by the Natural Sciences and Engineering Research Council of Canada is gratefully acknowledged. In addition, thanks are due to NATO for an International Scientific Exchange Award and to CNRS. The gift of several substituted pyridines and other amines by Reilly Tar and Chemical Company is also acknowledged with thanks.

Keywords

DMAP
dialkylaminopyridine
microenvironment effect
polymer-bound catalyst
synthesis

ASJC Scopus subject areas

Organic Chemistry
Polymers and Plastics
Materials Chemistry

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10.1016/0032-3861(87)90235-7

Cite this

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title = "Synthesis of new dialkylaminopyridine acylation catalysts and their attachment to insoluble polymer supports",

abstract = "Dialkylaminopyridines whose N-substituents bear a hydroxyl or amino group can be made economically from 4-cyanopyridine. Simple but selective alkylation of these compounds with commercial (chloromethyl) or (3-bromopropyl) polystyrene gives several new solid-phase catalysts which are highly active in promoting the acylation of hindered alcohols. Comparison of syntheses and reactivities, among these and some other heterocyclic polymers, illustrates several useful general principles of reactive polymer chemistry such as local concentration and microenvironment effects.",

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author = "Andr{\'e} Deratani and Darling, {Graham D.} and Fr{\'e}chet, {Jean M.J.}",

note = "Funding Information: Financial support of this research by the Natural Sciences and Engineering Research Council of Canada is gratefully acknowledged. In addition, thanks are due to NATO for an International Scientific Exchange Award and to CNRS. The gift of several substituted pyridines and other amines by Reilly Tar and Chemical Company is also acknowledged with thanks.",

year = "1987",

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doi = "10.1016/0032-3861(87)90235-7",

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T1 - Synthesis of new dialkylaminopyridine acylation catalysts and their attachment to insoluble polymer supports

AU - Deratani, André

AU - Darling, Graham D.

AU - Fréchet, Jean M.J.

N1 - Funding Information: Financial support of this research by the Natural Sciences and Engineering Research Council of Canada is gratefully acknowledged. In addition, thanks are due to NATO for an International Scientific Exchange Award and to CNRS. The gift of several substituted pyridines and other amines by Reilly Tar and Chemical Company is also acknowledged with thanks.

PY - 1987/4

Y1 - 1987/4

N2 - Dialkylaminopyridines whose N-substituents bear a hydroxyl or amino group can be made economically from 4-cyanopyridine. Simple but selective alkylation of these compounds with commercial (chloromethyl) or (3-bromopropyl) polystyrene gives several new solid-phase catalysts which are highly active in promoting the acylation of hindered alcohols. Comparison of syntheses and reactivities, among these and some other heterocyclic polymers, illustrates several useful general principles of reactive polymer chemistry such as local concentration and microenvironment effects.

AB - Dialkylaminopyridines whose N-substituents bear a hydroxyl or amino group can be made economically from 4-cyanopyridine. Simple but selective alkylation of these compounds with commercial (chloromethyl) or (3-bromopropyl) polystyrene gives several new solid-phase catalysts which are highly active in promoting the acylation of hindered alcohols. Comparison of syntheses and reactivities, among these and some other heterocyclic polymers, illustrates several useful general principles of reactive polymer chemistry such as local concentration and microenvironment effects.

KW - DMAP

KW - dialkylaminopyridine

KW - microenvironment effect

KW - polymer-bound catalyst

KW - synthesis

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DO - 10.1016/0032-3861(87)90235-7

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JF - Polymer

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Synthesis of new dialkylaminopyridine acylation catalysts and their attachment to insoluble polymer supports

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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