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Conversion of phenyl-substituted cyclopentadienes to pyrylium cations
Gui Ling Ning1, Xin Cheng Li, Megumu Munakata
1School of Chemical Engineering, Dalian University of Technology, Dalian 116012, PR China. ninggl@dlut.edu.cn
The Journal of Organic Chemistry
|February 14, 2004
Abstract:
Phenyl-substituted cyclopentadienes are proved to form phenylated pyrylium cations in the presence of silver(I) perchlorate by insertion of an oxygen atom into the cyclopentadiene-ring. Three phenylated pyrylium compounds, [(Ph(5)C(5)O(+))(ClO(4)(-))](2)(CH(2)Cl(2)) (1), Ag(ClO(4))(H(2)O)(Ph(4)HC(5)O(+)) (ClO(4)(-)) (2), and (Ph(3)H(2)C(5)O(+))(ClO(4)(-)) (3) have been synthesized and characterized. A possible reaction pathway and formation mechanism of the pyrylium cation are proposed and discussed.