Journal
ORGANIC LETTERS
Volume 16, Issue 11, Pages 2920-2922Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol5010627
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Funding
- National Science Foundation [CHE-1147787, CHE-1062944]
- Camille and Henry Dreyfus Foundation
- Colby College
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1147787] Funding Source: National Science Foundation
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Oxacalixarenes bearing acetylene groups are synthesized in a single step by nucleophilic aromatic substitution reactions of orcinol with various 1,5-diethynyl-2,4-difluorobenzenes. Thermodynamic equilibration of the cyclooligomer mixtures was accomplished for arylethynyl activating groups, leading to increased yields of the corresponding oxacalix[4]arenes. A 1,3-alternate macrocycle conformation is observed in the solid state, presenting a large V-shaped pi-surface.
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