Control of the Intramolecular [2+2] Photocycloaddition in a Bis-Stilbene Macrocycle

被引：29
|
作者：
Xu, Yuewen [1 ]
Smith, Mark D. [1 ]
Krause, Jeanette A. [2 ]
Shimizu, Linda S. [1 ]
机构：
[1] Univ S Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA
[2] Univ Cincinnati, Dept Chem, Richard C Elder Xray Crystallog Facil, Cincinnati, OH 45221 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 13期
关键词：
CIS-TRANS-PHOTOISOMERIZATION; SOLID-STATE; 2-PI+2-PI PHOTOCYCLOADDITION; PHOTOCHEMICAL CYCLOADDITION; PHOTODIMERIZATION; DISCRETE; TEMPLATE; ACID;
D O I：
10.1021/jo900443e
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The intramolecular [2+2] photocyclization of a bis-stilbene macrocycle was studied. The reaction call be controlled by the insertion and removal of urea protecting groups. Upon UV-irradiation in both the solid state and DMSO solution, the free urea macrocycle undergoes a cis-trans photoisomerization that is followed by a [2+2] cycloaddition to afford a single product in high yield. The presence of the triazinanone urea protecting groups does not alter the cis-trans photoisomerization but greatly decreases the selectivity of the photocycloaddition step.
引用
收藏
页码：4874 / 4877
页数：4
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