Synthesis of tri-arylated cyclotriveratrilenes with ortho- and meta-extended functionality

[Display omitted] Aromatic nucleophilic substitution reaction between cyclotriguaiacylene and ortho- or meta-functionalized fluoroarenes affords a series of ortho- or meta-extended cyclotriveratrilene (CTV) cavitands. Further transformation of the functional groups into NH and/or OH moieties has bee...

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Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 2; pp. 233 - 236
Main Authors Ito, Kouhei, Schramm, Michael P., Kanaura, Mao, Ide, Masataka, Endo, Naoki, Iwasawa, Tetsuo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.01.2016
Elsevier
Subjects
Chemistry
Chemistry, Organic
Cyclotriguaiacylene
Cyclotriveratrilene
Introverted functionality
Physical Sciences
Science & Technology
Supramolecular capsule
Water-soluble cavitand
Introverted functionality
Cyclotriveratrilene
Cyclotriguaiacylene
Supramolecular capsule
Water-soluble cavitand
CATALYSIS
CHOLINE
REACTIVITY
IRON(II)
DEEP CAVITAND
LIGANDS
AMINES
MOLECULAR RECOGNITION
MONOALKYLATION
HEMICRYPTOPHANE
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Summary:[Display omitted] Aromatic nucleophilic substitution reaction between cyclotriguaiacylene and ortho- or meta-functionalized fluoroarenes affords a series of ortho- or meta-extended cyclotriveratrilene (CTV) cavitands. Further transformation of the functional groups into NH and/or OH moieties has been demonstrated. This enabled us to prepare an amphoteric water-soluble cavitand bearing anilino-NH2 and phenolic-OH substituents. In addition, one molecular structure was successfully determined by crystallographic analysis, which suggests an extended/flattened structure. We propose that vase-shaped conformations with inwardly directed functional groups will soon be possible with the CTV scaffold.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.12.030