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Bridging of Resorcin[4]arenes in the Chair Conformation to Cavitands Having Two Pairs of Axial and Equatorial Substituents

Authors :
Huub Kooijman
and Anthony L. Spek
Oskar Middel
Ron Hulst
Willem Verboom
David N. Reinhoudt
Faculty of Science and Technology
Molecular Nanofabrication
Source :
Journal of organic chemistry, 63(63), 8259-8265. American Chemical Society
Publication Year :
1998
Publisher :
American Chemical Society (ACS), 1998.

Abstract

3-7 with bromochloromethane. According to X-ray analysis of cavitand 19 and 1-D and 2-D NMR spectroscopy for 18, the cavitands possess a stereochemistry with two adjacent aryl substituents in the axial position and the two others in the equatorial position. The starting methylresorcin-[4]arenes 3-7 were obtained exclusively in the chair conformation in 30-98% yield upon condensation of 2-methylresorcinol with aryl aldehydes.

Details

ISSN :
15206904 and 00223263
Volume :
63
Database :
OpenAIRE
Journal :
The Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....3c1352a68d6ebaba404915f37feb9b35
Full Text :
https://doi.org/10.1021/jo9810258