Study On Dual Properties Of Sydnoyl Ring Via Electrophilic Reactions

• Main Authors: Chen, Kaifeng, 陳凱鋒
• Other Authors: Lin, Shawdao
• Format: Others
• Language: zh-TW
• Published: 2012
• Online Access: http://ndltd.ncl.edu.tw/handle/03773010582292516873

碩士 === 靜宜大學 === 應用化學系 === 100 === Under this study, we used either the electron-donor to activate to compensate the nature of the electron-withdrawn chacter of N(3)or inserted the methylene group(s) between N(3) and phenyl to diminish the drawn ability of N(3).From the product distribution of nitration and bromination (partial) we are able to demonstrate the dual properties that the electron-donating nature of C(4) and the electron-withdrawn character of N(3). The later can be compensated by either the presence of an electron-donor on the phenyl group or isolated by adding the methylene group between N(3) and phenyl ring. Nitro group processes as a strong electrophilic reagent and attacks at phenyl ring of benzyl group at N(3) position. The formation of the disubstitured product was also observed due to the nitration at the C(4) position of benzyl sydnone. Furthermore, the presence of electron donor, such as methyl or methoxy, enhances the electrophilicily to lead in the competition for forming the double nitrationon the phenyl ring.