Stereoselective formation of dicondensed spiropyran product obtained from the reaction of excess Fischer base with salicylaldehydes: first full characterization by X-ray crystal structure analysis of

详细信息    查看全文

• 作者：Keum ; Sam-Rok ; Ku ; Byung-Soo ; Shin ; Jin-Taek ; Ko ; Jae Jung ; Buncel ; Erwin
• 关键词：Dicondensed spiropyran ; Single crystal X-ray diffraction analysis ; Stereoselective formation ; Cyclic carbinol intermediate ; Intramolecular H-bonding
• 刊名：Tetrahedron
• 出版年：2005
• 出版时间：July 11, 2005
• 年：2005
• 卷：61
• 期：28
• 页码：6720-6725
• 全文大小：285 K

文摘

The structure and stereochemistry of the dicondensed spiropyran product (DC-1, X=COOH) obtained from reaction of excess Fischer base with substituted salicylaldehydes has been fully assigned as C with (8R, 10R) configuration on the basis of single crystal X-ray diffraction analysis. The stereoselective formation of DC molecules indicates that the most plausible mechanism for DC formation involves dehydration of the cyclic carbinol intermediate with the aid of intramolecular H-bonding via transition structure TS₁^‡.