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Relative reactivity of primary and secondary amine hydrogen atoms in the reaction between aniline and phenyl glycidyl ether: The effect of ethanol and other additives and the modifying effect of benzene as solvent

1989; Wiley; Volume: 27; Issue: 2 Linguagem: Inglês

10.1002/pola.1989.080270223

1099-0518

Peter Johncock,

Organic and Inorganic Chemical Reactions

Abstract The relative reactivity ratio ( k 2 / k 1 ) for the secondary and primary amine hydrogen atoms in the neat reaction between aniline and phenyl glycidyl ether was 0.30. This is significantly lower than a recently reaffirmed random value of 0.5 for this system. The ratio is sensitive to added ethanol and decreased with increasing concentration to a limiting value of about 0.20. With benzene as solvent, the effect of added ethanol was more complex, and a low concentration provided a value of 0.45 which decreased with increasing concentration. Other hydroxy additives behaved similarly, but boron trifluoride appears to have no effect on this ratio.