Studies of the 1,3-dipolarcycloaddition reaction of sydnone derivative and dicyclopentadiene

• Main Authors: Shui-Man Huang, 黃秀滿
• Other Authors: Shaw-Tao Lin
• Format: Others
• Language: zh-TW
• Published: 2001
• Online Access: http://ndltd.ncl.edu.tw/handle/13173189538351991818

碩士 === 靜宜大學 === 應用化學系 === 90 === Abstract Sydnone is a typical mesoionic compound and a five-membered non-benzoid aromatic heterocyclic compound. The electronic constraction and special reactivities of the sydnone ring can be applied as a precurso to transform to other heterocyclic compounds. This study focus on 1,3-dipolar cycloaddition from sydnone compound and cyclopentadiene and/or dicyclopentadiene. This cycloaddition prefer to proceed in the non-polar system, such as xylene. Four compounds, i.e., 2-phenyl-5,8-methano-1,2,3a,4,7,7a-hexahydroindeno(1-2,c)-4,5-dihydropyrazole(59)；2-phenyl-4,8-methanocyclopenteno(4-3,f)-hexahydro- 2H,3H-inda-zole(60)；1-phenylpyrazolino(4-3,d)cyclopentene(61)；2-phenyl-4,7-methano-1,2,2a,3,6,6a-hexahydroindeno(1-2,c)pyrazole(62) are isolated and are identified through a series of NMR spectroscopic studies and also verified by x-ray analyses. Compounds can be formed from direct addition of either bicyclopentadiene or double addition of cyclopentadiene. The pyrrol ring in those products undergo deprotonation to yield ,i.e.,2-phenyl-5,8-methano-2,4,4a,5,8,8a-hexa hydro-indeno(1-2,c) pyrazole (63) in weak acidic solution (ex: CDCl3) under room temperature.