2253-15-8Relevant academic research and scientific papers
A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF3SiMe3 as a trifluoromethylating agent
Masusai, Chonticha,Soorukram, Darunee,Kuhakarn, Chutima,Tuchinda, Patoomratana,Pakawatchai, Chaveng,Saithong, Saowanit,Reutrakul, Vichai,Pohmakotr, Manat
, p. 6650 - 6658 (2013/09/24)
A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) to a masked maleic anhydride 1 (cyclopentadiene-maleic anhydride adduct) provides the corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis.
Convenient Preparations and Michael Reactions of 4-Fluoroalkylated But-2-en-4-olides
Yoshida, Masato,Imai, Rihoko,Komatsu, Yuji,Morinaga, Yoshihiro,Kamigata, Nobumasa,Iyoda, Masahiko
, p. 501 - 504 (2007/10/02)
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.
