Zoltewicz

The kinetic aspects of the Sn2 quaternization (the Menschutkin reaction) have been covered by Zoltewicz and Deady (78AHC(22)72), the latter author having done most of the experimental work related to pyrazoles and indazoles. In C-unsubstituted methyl deriva-... 

E. C. Taylor, Princeton, New Jersey M. Tisler, Ljubljana, Slovenia J. A. Zoltewicz, Gainesville, Florida... 

R. A. Abramovitch, Clemson, South Carolina A. T. Balaban, Bucharest, Romania A. J. Boulton, Norwich, England H. Dorn, Berlin, Germany J. Elguero, Madrid, Spain S. Gronowitz, Lund, Sweden O. Meth-Cohn, Sunderland, England C. W. Rees, FRS, London, England E. C. Taylor, Princeton, New Jersey M. Tisler, Ljubljana, Slovenia J. A. Zoltewicz, Gainesville, Florida... 

Zoltewicz and Oestreich (1973) employed sodium methylate to accelerate the reaction between 4-bromo-iso-quinoline and sodium thiophenolate. In this case, the CHjO ion acts as a competing electron donor with respect to the PhS ion. On electron transfer to the substrate, thiophenolate converts into the phenylthiyl radical and then to diphenyldisulhde. Diphenyldisulfide is inactive in further transformations. The methylate ions generate the anion-radicals of the substrate, thus preserving the greater part of the thiophenolate for use in substitution. The observed rate of thioarylation and the yield of 4-phenylthio-iso-quinoline increase in the presence of sodium methylate. Azobenzene inhibits the action of sodium methylate. Scheme 5.7 summarizes what has been mentioned. 

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