Document Detail

Synthesis of large [2]rotaxanes. The relationship between the size of the blocking group and the stability of the rotaxane.
MedLine Citation:
PMID:  23541290     Owner:  NLM     Status:  MEDLINE    
[2]Rotaxanes with large macrocyclic phenanthrolines were prepared by the template method, and the stability of the rotaxanes was examined. Compared to the tris(biphenyl)methyl group, the tris(4-cyclohexylbiphenyl)methyl group was a larger blocking group, and the rate of the dissociation of the components decreased significantly when the thermal stability of a rotaxane with a 41-memebered ring was examined. We also succeeded in the synthesis of larger rotaxanes by the oxidative dimerization of alkynes with these bulky blocking groups, utilizing the catalytic activity of the macrocyclic phenanthroline-Cu complex.
Shinichi Saito; Eiko Takahashi; Kouta Wakatsuki; Kazuhiko Inoue; Tomoko Orikasa; Kenta Sakai; Ryu Yamasaki; Yuichiro Mutoh; Takeshi Kasama
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2013-04-11
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  78     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2013 Apr 
Date Detail:
Created Date:  2013-04-19     Completed Date:  2013-08-12     Revised Date:  2013-08-30    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3553-60     Citation Subset:  IM    
Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku, Tokyo 162-8601, Japan.
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MeSH Terms
Copper / chemistry*
Macrocyclic Compounds / chemical synthesis*,  chemistry*
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Organometallic Compounds / chemical synthesis*,  chemistry*
Phenanthrolines / chemistry*
Rotaxanes / chemical synthesis*,  chemistry*
Reg. No./Substance:
0/Macrocyclic Compounds; 0/Organometallic Compounds; 0/Phenanthrolines; 0/Rotaxanes; 7440-50-8/Copper
Erratum In:
J Org Chem. 2013 Jun 7;78(11):5816

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