Vinyl Nucleophilic Substitution. II. Interaction of Cyclopentadienylcarbonyliron Anion with β-Halo-α,β-Difluorostyrenes. Ion Association Effectстатья
Информация о цитировании статьи получена из
Web of Science
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 27 мая 2015 г.
Аннотация:In the reaction of CpFe(CO)2K with α,β,β-trifluorostyrene and Z- and E-isomers of β-chloro-α,β-difluorostyrene besides the expected products of vinyl nucleophilic substitution, Z(E)-PhCF=CFFe(CO)2Cp, we found the products of a redox process, [CpFe(CO)2]2 and PhC≡CFe(CO)2Cp. Nucleophilic substitution of chlorine in Z- and E-isomers of β-chloro-α,β-difluorostyrene under the action of CpFe(CO)2K proceeds with retention of configuration at the double bond. The reaction rate of CpFe(CO)2K with α,β,β-trifluorostyrene and Z-β-chloro-α,β-difluorostyrene increases with increased medium polarity or on addition of 18-crown-6 ether, the same leads to a decrease of the yield of the dimer [CpFe(CO)2]2 formed concurrently. Stereochemistry and kinetics of these reactions fit to the commonly accepted addition-elimination mechanism.