Cucurbit[7]uril Mediates the Stereoselective [4+4] Photodimerization of 2-Aminopyridine Hydrochloride in Aqueous Solution

The 2:1 guest−host complex of 2-aminopyridine hydrochloride with cucurbit[7]uril (CB[7]) undergoes a stereoselective [4+4] photodimerization reaction in aqueous solution to yield exclusively the anti-trans isomer of 4,8-diamino-3,7-diazatricyclo[4.2.2.22,5]dodeca-3,7,9,11-tetraene, and in the absenc...

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Veröffentlicht in:	Journal of organic chemistry 2006-02, Vol.71 (3), p.1237-1239
Hauptverfasser:	Wang, Ruibing, Yuan, Lina, Macartney, Donal H
Format:	Artikel
Sprache:	eng
Schlagworte:	Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Organic chemistry Preparations and properties
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Zusammenfassung:	The 2:1 guest−host complex of 2-aminopyridine hydrochloride with cucurbit[7]uril (CB[7]) undergoes a stereoselective [4+4] photodimerization reaction in aqueous solution to yield exclusively the anti-trans isomer of 4,8-diamino-3,7-diazatricyclo[4.2.2.22,5]dodeca-3,7,9,11-tetraene, and in the absence of CB[7], the photochemical reaction produces the anti-trans and syn-trans photodimers in a 4:1 ratio. In addition, encapsulation of the photodimer product in the CB[7] cavity stabilizes it with respect to the otherwise observed rearomatization to the 2-aminopyridine monomer at room temperature.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo052136r