Thiophene series. Note IX . The absence of secondary steric effects in nucleophilic substitutions of thiophene derivatives: Kinetics of the reactions of 2‐bromo‐3,5‐dinitrothiophene and 2‐bromo‐3,5‐dinitro‐4‐methylthiophene with piperidine

Abstract

AbstractThe kinetics of the reactions of piperidine with 2‐bromo‐3,5‐dinitrothiophcne (IV) and 2‐bromo‐3,5‐dinitro‐4‐methylthiophene (III) have been measured in methanol, ethanol and benzene.Molecular model predictions were confirmed when the kinetic results (kIV/kIII ≅ 2) demonstrated, for the first time, the absence of secondary steric effects for nucleophilic substitutions in thiophene compounds.