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- W2146123934 abstract "Reaction of alkynyl(p-phenylene)bisiodonium ditriflateswithsodium phenoxide in methanol provides 2-substituted benzofurans in49–62% yields. This result indicates thatβ-phenoxyalkylidenecarbenes are generated by the reactionwith phenoxide anion and undergo novel intramolecular aromaticC–H insertion to afford benzofurans.2-Phenoxy-2-phenylethenylidene generated analogously in situunderwent competing processes of aromatic C–H insertion and1,2-phenyl migration. The corresponding reactions with 4-substitutedphenoxide ions also afforded 5-substituted benzofurans and, as the minorproducts, 2-aryloxy-1-iodoalk-1-enes which were probably derived fromthe intermediate vinyliodonium salts. Reactions ofalkynyl(p-phenylene)bisiodonium ditriflates with sodium[2H5]phenoxide (98% 2H) in methanolgave deuterated 2-alkylbenzofurans in 35–40% yields and thehydrogen at the 3-position of the benzofurans was deuterated completely.This result strongly supports selective aromatic C–H insertion ofthe in situ generatedβ-phenoxyalkylidenecarbenes." @default.
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- W2146123934 date "1997-01-01" @default.
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- W2146123934 title "Aromatic C–H insertion of β-phenoxyalkylidenecarbenes generated by reaction of alkynyl(p-phenylene)bisiodonium ditrifluoromethanesulfonates (ditriflates) with phenoxide anions" @default.
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- W2146123934 doi "https://doi.org/10.1039/a700602k" @default.
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