Vicarious Nucleophilic Substitution in Nitroquinolines1)

Abstract

Abstract5‐Nitro‐, 6‐nitro‐, and 8‐nitroquinoline react with the carbanions of chloromethyl phenyl sulfone, chloro‐N,N‐dimethylmethanesulfonamide and substituted acetonitriles XCH2CN (X = OPh, SPh, Cl) giving products of the vicarious nucleophilic substitution of hydrogen predominantly or exclusively at positions 6, 5, and 7, respectively. A different orientation pattern and sometimes other reaction pathways are observed in reactions involving tertiary carbanions of (phenoxy)(phenyl)acetonitrile and 1‐chloropropyl p‐tolyl sulfone. The 1H NMR spectra of the substitution products are discussed in connection with their structures.