Organic Letters 2006-06-22

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

Jeffrey L Katz, Bram J Geller, Rebecca R Conry

Index: Org. Lett. 8 , 2755, (2006)

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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.