Triphenylphosphonium-stoppered [2]rotaxanes

Stuart J. Rowan; Stuart J. Cantrill; J. Fraser Stoddart

doi:10.1021/ol990049d

Triphenylphosphonium-stoppered [2]rotaxanes

Stuart J. Rowan, Stuart J. Cantrill, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

85 Scopus citations

Abstract

(equation presented) The template-directed syntheses of two [2]rotaxanes, one carrying one and the other two triphenylphosphonium stoppers, have been achieved using a threading-followed-by-stoppering approach. Either one or two benzylic bromide functions-located at the para-positions of dibenzylammonium-based ions, which become encircled by dibenzo[24]crown-8 macrocycles during the initial thermodynamically controlled phases that mark the recognition events-serve as sites for nucleophilic attack by triphenylphosphine during the subsequent kinetic stages that lead to the formation of the two [2]rotaxanes.

Original language	English (US)
Pages (from-to)	129-132
Number of pages	4
Journal	Organic Letters
Volume	1
Issue number	1
DOIs	https://doi.org/10.1021/ol990049d
State	Published - Jul 15 1999

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Triphenylphosphonium-stoppered [2]rotaxanes",

abstract = "(equation presented) The template-directed syntheses of two [2]rotaxanes, one carrying one and the other two triphenylphosphonium stoppers, have been achieved using a threading-followed-by-stoppering approach. Either one or two benzylic bromide functions-located at the para-positions of dibenzylammonium-based ions, which become encircled by dibenzo[24]crown-8 macrocycles during the initial thermodynamically controlled phases that mark the recognition events-serve as sites for nucleophilic attack by triphenylphosphine during the subsequent kinetic stages that lead to the formation of the two [2]rotaxanes.",

author = "Rowan, {Stuart J.} and Cantrill, {Stuart J.} and Stoddart, {J. Fraser}",

year = "1999",

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AU - Rowan, Stuart J.

AU - Cantrill, Stuart J.

AU - Stoddart, J. Fraser

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N2 - (equation presented) The template-directed syntheses of two [2]rotaxanes, one carrying one and the other two triphenylphosphonium stoppers, have been achieved using a threading-followed-by-stoppering approach. Either one or two benzylic bromide functions-located at the para-positions of dibenzylammonium-based ions, which become encircled by dibenzo[24]crown-8 macrocycles during the initial thermodynamically controlled phases that mark the recognition events-serve as sites for nucleophilic attack by triphenylphosphine during the subsequent kinetic stages that lead to the formation of the two [2]rotaxanes.

AB - (equation presented) The template-directed syntheses of two [2]rotaxanes, one carrying one and the other two triphenylphosphonium stoppers, have been achieved using a threading-followed-by-stoppering approach. Either one or two benzylic bromide functions-located at the para-positions of dibenzylammonium-based ions, which become encircled by dibenzo[24]crown-8 macrocycles during the initial thermodynamically controlled phases that mark the recognition events-serve as sites for nucleophilic attack by triphenylphosphine during the subsequent kinetic stages that lead to the formation of the two [2]rotaxanes.

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Triphenylphosphonium-stoppered [2]rotaxanes

Abstract

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