Reaction of perfluorocyclopentene with various carbon nucleophiles--heteroaromatic lithium reagents, enolate and phosphonium ylide.
The addition of heteroaromatic lithium reagents 2 to a THF solution of perfluorocyclopentene (1) provided preferentially the corresponding monosubstituted products 5, while the addition of 1 to 2 effectively gave the 1,2-disubstituted products 6 in good to excellent yields. The reaction of 1 with sodiomalonate 3 or phosphonium ylide 4 also proceeded smoothly to form the 1,3-disubstituted product 8 or 10 in high yield, respectively.
Yamada
Shigeyuki
S
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan.
Ishii
Emi
E
Konno
Tsutomu
T
Ishihara
Takashi
T
D000098:Acetophenones / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry*; D018020:Lithium Compounds / Q000737:chemistry*; D008314:Malonates / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*
D000098:Acetophenones; D003517:Cyclopentanes; D005466:Fluorocarbons; D018020:Lithium Compounds; D008314:Malonates; D009943:Organophosphorus Compounds; C521095:perfluorocyclopentene; C521096:triphenylphosphonium methylide; C498810:diethyl malonate; D002244:Carbon