60223-06-5Relevant articles and documents
ELECTROPHILIC ADDITION OF α-FLUOROALKYL ETHERS TO OLEFINS
Lebedev, M. Yu.,Balenkova, E. S.
, p. 235 - 239 (2007/10/02)
α-Fluoro ethers FCH2OR (R = Me, Et) enter into electrophilic addition with methylenecyclobutane, cyclohexene, cyclopentene, and 1-hexene at room temperature in the absence of catalysts.The effect of the solvents and the reagent ratio on the nature of the reaction were studied for the case of methylenecyclobutane.The reactions of α-fluoro ethers with methylenecyclobutane in methylene chloride, nitromethane, and sulfur dioxide lead to the formation of mixtures of the corresponding 1-fluoro-1-(2-alkoxyethyl)cyclobutanes, 1-alkoxy-1-(2-alkoxyethyl)cyclobutanes, and (1-methylcyclobutyl)methylenecyclobutane. 1-Methoxy-1-(2-methoxyethyl)cyclobutane is the only product from the reaction with an excess of the fluoro ether FCH2OMe with methylenecyclobutane.The products from the reaction of α-fluoro ethers with cyclohexene and 1-hexene are 3-alkoxymethylcyclohexenes and mixtures of cis- and trans-1-alkoxy-3-heptenes.Under the same conditions cycloheptene and α-fluoromethyl ether gave a mixture of 3-methoxymethylcyclopentene and cis- and trans-1-fluoro-2-methoxymethylcyclopentanes.