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Paper | Regular issue | Vol 53, No. 4, 2000, pp.877-886
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8827
Mechanism on One-sided Wessely-Moser Rearrangement Reaction

Kazuki Shinomiya, Yoshio Hano, and Taro Nomura*

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Wessely-Moser rearrangement reaction of 5,7-dihydroxychromone derivatives with an isopentyl side chain at C-6 or C-8 position was examined. All reactions gave 8-isopentylchromone derivative predominantly as rearrangement product. Kinetic analysis of the one-sided rearrangement reaction revealed that the reaction depends on stability of a flavylium cation originated from 8-isopentylchromone derivative.