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Syntheses and conformations of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides

Authors
No, KLee, JHYang, SHYu, SHCho, MHKim, MJKim, JS
Issue Date
May-2002
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.67, no.9, pp 3165 - 3168
Pages
4
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
Volume
67
Number
9
Start Page
3165
End Page
3168
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/16415
DOI
10.1021/jo011138i
ISSN
0022-3263
1520-6904
Abstract
A series of tetrahomodioxacalix[4]arene tetraamides and tetrathioamides with four p-phenyl groups on their upper rim were synthesized. From the H-1 and C-13 NMR and crystal structure, N-butylamido homooxacalix[4]arene (4) was found to be in the 1,3-alternate conformation and has intramolecular hydrogen bonding between N-H and facing oxygen atoms of the carbonyl O=C group. This hydrogen bonding decreased the metal ion complex ability. Transformation of the 1,3-alternate N-butylamido (4) into N-butylthioamido homooxacalix[4]arene (5) using Lawesson's reagent gave a conformational change to the C-1,2-alternate.
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