Reaction of perfluorocyclopentene with various carbon nucleophiles--heteroaromatic lithium reagents, enolate and phosphonium ylide.
Shigeyuki Yamada, Emi Ishii, Tsutomu Konno, Takashi Ishihara
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585, Japan.
Organic & biomolecular chemistry 2007 May 7The 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.
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Shigeyuki Yamada, Emi Ishii, Tsutomu Konno, Takashi Ishihara. Reaction of perfluorocyclopentene with various carbon nucleophiles--heteroaromatic lithium reagents, enolate and phosphonium ylide. Organic & biomolecular chemistry. 2007 May 7;5(9):1442-9
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PMID: 17464414
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