1987 Volume 60 Issue 3 Pages 1097-1101
The label scrambling within the ethylene chain of the final acetolysis products was determined for a series of α-D2 labeled 2-arylethyl tosylates by using proton NMR spectroscopy and the kΔ⁄ks values were derived from the scrambling ratios. For both buffered and unbuffered acetolysis runs log (kΔ⁄ks) were not correlated linearly with σ° or σ+. Application of the LArSR Eq. results in linear correlations with excellent precision, log (kΔ⁄ks)=−3.70 (σ°+0.63Δ\barσR+)+0.152 for the unbuffered run and log (kΔ⁄ks)=−3.97 (σ°+0.60Δ\barσR+)−0.207 for the buffered run. The ρΔ and rΔ values for the aryl-assisted pathway are estimated from the above apparent values based on the reasonable assumption of small ρs values for the ks pathway.
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