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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.


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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