Cyclization of p-tert-butylcalix[6]arene with diols under the mitsunobu protocol. A conformational study of the peralkylated derivatives

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Abstract

p-tert-Butylcalix[6]arene was attempted to O-alkylate with alcohols and diols under the Mitsunobu protocol. Regio-and conformation-selective reactions were not observed with alcohols and oligoethylene glycols, but 1, 6-hexaneand 1, 8-octanediols effected cone-selective A, D-bridging. Exhaustive alkylation of the remaining four OH groups in a cyclized molecule was carried out under base-promoted conditions and the conformation of the products along with the metal ion binding properties were studied by NMR methods.

Original languageEnglish
Pages (from-to)311-315
Number of pages5
JournalLetters in Organic Chemistry
Volume6
Issue number4
DOIs
Publication statusPublished - Jun 2009

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Cyclization
Conformations
Alcohols
Derivatives
Glycols
Alkylation
Metal ions
Cones
Metals
Nuclear magnetic resonance
Ions
Molecules

Keywords

  • Calix[6]arene
  • Cation binding
  • Conformation
  • Mitsunobu cyclization
  • O-Alkylation

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

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abstract = "p-tert-Butylcalix[6]arene was attempted to O-alkylate with alcohols and diols under the Mitsunobu protocol. Regio-and conformation-selective reactions were not observed with alcohols and oligoethylene glycols, but 1, 6-hexaneand 1, 8-octanediols effected cone-selective A, D-bridging. Exhaustive alkylation of the remaining four OH groups in a cyclized molecule was carried out under base-promoted conditions and the conformation of the products along with the metal ion binding properties were studied by NMR methods.",
keywords = "Calix[6]arene, Cation binding, Conformation, Mitsunobu cyclization, O-Alkylation",
author = "A. Gr{\"u}n and B. Bal{\'a}zs and I. Bitter",
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T1 - Cyclization of p-tert-butylcalix[6]arene with diols under the mitsunobu protocol. A conformational study of the peralkylated derivatives

AU - Grün, A.

AU - Balázs, B.

AU - Bitter, I.

PY - 2009/6

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AB - p-tert-Butylcalix[6]arene was attempted to O-alkylate with alcohols and diols under the Mitsunobu protocol. Regio-and conformation-selective reactions were not observed with alcohols and oligoethylene glycols, but 1, 6-hexaneand 1, 8-octanediols effected cone-selective A, D-bridging. Exhaustive alkylation of the remaining four OH groups in a cyclized molecule was carried out under base-promoted conditions and the conformation of the products along with the metal ion binding properties were studied by NMR methods.

KW - Calix[6]arene

KW - Cation binding

KW - Conformation

KW - Mitsunobu cyclization

KW - O-Alkylation

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