Reaction of selenofenchone with propiolic acid: first instance of Wagner-Meerwein rearrangement in selone |
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| Authors: | Kentaro Okuma Yuichi Mori Miki Tabuchi Yoshinobu Yokomori |
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| Institution: | a Department of Chemistry, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan
b National Defense Academy, Hashirimizu, Yokosuka 239-8686, Japan |
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| Abstract: | The reaction of selenofenchone (3a) with propiolic acid in refluxing chloroform produced selenodioxenone (4) along with rearranged product (5b), while 5b was obtained in almost quantitative yield under solvent-free conditions. In the presence of Lewis acid, selenofenchone 3a reacted with methyl propiolate to afford corresponding rearranged adduct (7). |
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