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Org Lett. 2006 Jun 22;8(13):2755-8. doi: 10.1021/ol060823e.

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

Organic letters

Jeffrey L Katz, Bram J Geller, Rebecca R Conry

Affiliations

  1. Department of Chemistry, Colby College, Waterville, Maine 04901, USA. [email protected]

PMID: 16774249 DOI: 10.1021/ol060823e

Abstract

[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.

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