期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2010, 期 33, 页码 6464-6470出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000718
关键词
Conformation analysis; Cyclocondensation; Cyclooligomerization; Host-guest chemistry; Regioselectivity
资金
- National Science Foundation of China [20872038]
- Specialized Chinese Research Fund for the Doctoral Program of Higher Education [20060561024]
The catalytic cyclocondensation of 1-butoxy-4-methoxy-2,5-bis(methoxymethyl)benzene (1d) affords a statistical mixture of the regioisomeric pillar[5]arenes 3a-d in high yield. The alkoxy groups are arranged stereoselectively in a mode so that they avoid steric interactions. The rotation of the benzene rings is, at room temperature, fast in terms of the NMR timescale and leads to a de facto C-s symmetry for 3a-c and a C-5h symmetry for 3d. All four structural isomers can encapsulate two CH3CN guest molecules. The structure determinations are based on four crystal structure analyses (constitutions) and NMR spectroscopic measurements (conformations).
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