Changes of selectivity in the reactions of substituted 4-nitrobenzyl sulfonates with nucleophilic reagents

P Dietze, WP Jencks

Index: Dietze, Paul; Jencks, William P. Journal of the American Chemical Society, 1989 , vol. 111, # 15 p. 5880 - 5886

Full Text: HTML

Citation Number: 14

Abstract

Abstract: The selectivities for anionic nucleophilic reagents are larger for reaction with 4- nitrobenzyl mesylate than with the corresponding triflate. Selectivities were determined over a range of rate constants of-lo4 for nucleophiles and-los for 4-nitrobenzyl sulfonates in 2030 CH3CN/HOH (v: v) at 25 OC, ionic strength 0.5 M (NaC10,). The slope of a correlation of log (kN/kHOH) for the two compounds is 1.12. Larger increases in selectivity of up to 11-fold ...