Reactions of SO2X mono-substituted arenes with SO3 in nitromethane: electronic and steric directing effects of the sulfonic acid group and some model substituents

…, EJD Graaf, E Zelvelder, H Cerfontain

Index: Ansink, Harold R. W.; Graaf, Erik J. de; Zelvelder, Erwin; Cerfontain, Hans Canadian Journal of Chemistry, 1993 , vol. 71, # 2 p. 210 - 215

Full Text: HTML

Citation Number: 2

Abstract

The sulfonation of benzene-SO2X (X= CH3, OCH3, OH, and Cl) and of 1-and 2-naphthalene- SO2X (X= CH3, OCH3, and Cl) with sulfur trioxide in nitromethane as solvent has been studied. In the benzene series, substitution only occurs at the 3-position irrespective of X; the reaction rates, which are all within the same order of magnitude, are low. Upon sulfonation of the 1-SO2X-substituted naphthalenes, the main sulfonation product (58-80%) is the 5- ...