Single step synthesis of acetylene-substituted oxacalix[4]arenes.
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 π-surface.
Department of Chemistry, Colby College , 5754 Mayflower Hill, Waterville, Maine 04901, United States.
Jay Wm
JW
Wackerly
Mengfei
M
Zhang
Stephen T
ST
Nodder
Stephen M
SM
Carlin
Jeffrey L
JL
Katz