Ring-Opening Reactions. 31. Mechanistic Path vs. Ring Strain Control in Elimination and Substitution Reactions of 1,1-Dimethyl Cyclic Ammonium Ions and Their α,α'-Dimethyl-Substituted Derivatives

Article abstract of DOI:10.1021/jo00327a021

From the determination of product composition and overall second-order rate constants for the reactions of a number of cyclic quaternary ammonium ions with sodium methoxide in methanol and previous similar data, a complete set of partial rate coefficients for the ring-opening reactions (substitution and elimination) of 1,1-dimethyl cyclic ammonium ions and their α,α'-dimethyl-substituted derivatives for ring sizes 4-6 was made available.Such reactions are sensitive probes for steric strain and reaction mechanism requirements in the β-elimination reaction and for thedifferent stereochemical requirements of elimination vs. substitution.