Journal of the Chemical Society. Perkin transactions I p. 501 - 504 (1993)
Update date:2022-08-04
Topics:
Yoshida, Masato
Imai, Rihoko
Komatsu, Yuji
Morinaga, Yoshihiro
Kamigata, Nobumasa
Iyoda, Masahiko
Trifluoromethyl, heptafluoropropyl and chlorodifluoromethyl substituted but-2-en-4-olides have been prepared both from 2-trimethylsiloxyfuran by fluoroalkylation with the corresponding bis(fluoroalkanoyl) peroxide and from 2-fluoroalkylfuran by oxidation with m-nitrobenzenesulfonyl peroxide. 4-Difluoromethylbut-2-en-4-olide was also prepared by chlorodifluoromethylation of 2-methoxyfuran followed by reduction of the chlorine.The 4-trifluoromethylated butenolide thus prepared, could be readily converted into the anion by treatment with weak base.The anion so formed then reacted with electron-deficient olefins to give 4,4-disubstituted butenolides.
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