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Synthesis of oxacalixarenes incorporating nitrogen heterocycles: evidence for thermodynamic control.

Katz JL, Geller BJ, Conry RR

Department of Chemistry, Colby College, Waterville, Maine 04901, USA. jlkatz@colby.edu

[structure: see text] Oxacalix[2]arene[2]hetarenes are formed in a single step by cyclooligomerization of meta-diphenols with meta-dichlorinated azaheterocycles. The high selectivity for cyclic tetramer formation results from thermodynamic product control. Macrocycles as large as oxacalix[5]arene[5]hetarenes have been isolated under nonequilibrating conditions.

Published 15 June 2006 in Org Lett, 8(13): 2755-8.
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