Convenient preparations and Michael reactions of 4-fluoroalkylated but-2-en-4-olides
摘要:
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-methoxy-furan 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.
Chlorodifluoromethyl group was introduced into aromatic rings using bis(chlorodifluoroacetyl) peroxide which was readily prepared from corresponding acid anhydride with 30% hydrogen peroxide, and the chlorine was successively replaced by hydrogen or allyl group in excellent yields under radical conditions.
Method for production of fluorine-containing aromatic derivative
申请人:NIPPON OIL AND FATS COMPANY, LIMITED
公开号:EP0155093A2
公开(公告)日:1985-09-18
A fluorine-containing aromatic derivative useful as an intermediate for the synthesis of medicines, agricultural pesticides, and water-repellent oil-repellent agents is produced by a method characterized by causing a di(haloacyl)-peroxide of the general formula:
wherein X denotes a fluorine, chlorine, or hydrogen atom and n denotes an integer of the value of 1 to 10, to react with benzene, a mono-substituted benzene, naphthalene, or a mono-substituted naphthalene thereby introducing an X(CF2)n-group into the benzene ring or the naphthalene ring.