A Polyketone Synthesis Involving Nucleophilic Substitution via Carbanions Derived from Bis(α-aminonitrile)s. 5. A New, Well-Controlled Route to “Long” Bisphenol and Activated Aromatic Dihalide Monomers

Very efficient syntheses of “long” bisphenol and activated dihalide monomers containing keto groups were developed on the basis of α-aminonitrile chemistry. Known and novel activated dihalide monomers were obtained in quantitative yields and without isomeric impurities. This method is suitable for any activated dihalide by reaction with 2 equiv of the anion of p -fluorobenzalaminonitrile ( 8 ), followed by hydrolysis to produce a monomer with two more p -fluorobenzoyl units. Similarly, use of the anion of p -methoxybenzalaminonitrile ( 15 ) by reaction with activated dihalides provides a general route to bisphenols. Less expensive dichloro monomers, e.g., 4,4‘-dichlorobenzophenone, can be used to synthesize these “long” bisphenol and activated dihalide monomers.