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Abstract
Solvolysis Mechanism of cis ‐ and trans‐2‐Arylcylopentyl p‐Toluenesulfonates. The Step: 1‐Deuterium Isotope Effects, Basic Salt Effects, and Special Salt EffectWe have studied the first step of the solvolysis of cis and trans‐2‐arylcyclopentyl p‐toluenesulfonates in HCOOH, AcOH, and EtOh. All substrates show a high kinetic 1‐deuterium isotope effect (kH/kD(1) >1.15). This fact indicates that first step leads to classical intimate ion‐pair Which dissociates to a solvet‐separated ion‐pair, without participation either of solvent, the 2‐aryl group, or a H‐atom at C(2). The slight influence of added basic ions on reaction rate allows us to exclude any direct solvent attack on the covalent substrate even in the most favorable case, i.e. ethanolysis of 2‐(p‐nitrophenyl)cylopentyl‐p‐toluenesulfonates. Furthermore, solvent‐separated ion pair formation is indicated by the special salt effect induced by LiClO4.
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