The Cyclopentyl Group, As a Small but Bulky Terminal Group, Allows Rapid and Efficient Active Transport

Secondary ammonium salts bearing a cyclopentyl terminal group rapidly formed pseudorotaxane with 1.5 equiv of DB24C8. Acylation of the pseudorotaxane with 50 equiv of benzoyl chloride in the presence of 50 equiv of triethylamine in toluene afforded rotaxane, the product of active transport, in 95% y...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 1; pp. 138 - 141
Main Authors Nishiyama, Junya, Makita, Yoshimasa, Kihara, Nobuhiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.01.2015
Amer Chemical Soc
Subjects
Acylation
Biological Transport, Active
Chemistry
Chemistry, Organic
Cyclopentanes - chemical synthesis
Cyclopentanes - chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Physical Sciences
Rotaxanes - chemical synthesis
Rotaxanes - chemistry
Science & Technology
PSEUDOROTAXANE
ACYLATION
DRIVEN
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Summary:Secondary ammonium salts bearing a cyclopentyl terminal group rapidly formed pseudorotaxane with 1.5 equiv of DB24C8. Acylation of the pseudorotaxane with 50 equiv of benzoyl chloride in the presence of 50 equiv of triethylamine in toluene afforded rotaxane, the product of active transport, in 95% yield. The cyclopentyl group is small enough to allow rapid formation of pseudorotaxane, and bulky enough to facilitate the quantitative active transport by steric repulsion.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol5031469