Nucleophilic vinyl substitution reactions: V. Reaction of pentacarbonylrhenium anion with β-halo-α,β-difluorostyrenes. Effect of ion associationстатья
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Аннотация:α,β,β-Trifluorostyrene reacts with Re(CO)5Na along two competing pathways: nucleophilic vinyl substitution to give (Z)-PhCF=CFRe(CO)5 and radical chain reaction which leads to formation of (Z)-PhCF=CFRe(CO)4Re(CO)5Na. Tertiary phosphines and 2,6-di-tert-butyl-4-diphenylmethylene-2,5-cyclohexadienone as radical trap inhibit whereas Re2(CO)10 initiate the radical process, the nucleophilic substitution reaction remaining unaffected. The effects of solvent (THF, ether, acetonitrile) and 18-crown-6 on the direction and rate of the reaction suggest assistance to nucleophilic substitution by the cation.