Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Substituent Effects. XVII. Rearrangement in the Acetolysis of 2-Arylethyl Tosylates
Mizue FujioMutsuo GotoYoji SekiMasaaki MishimaYuho TsunoMasami SawadaYoshio Takai
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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 kΔks values were derived from the scrambling ratios. For both buffered and unbuffered acetolysis runs log (kΔks) were not correlated linearly with σ° or σ+. Application of the LArSR Eq. results in linear correlations with excellent precision, log (kΔks)=−3.70 (σ°+0.63Δ\barσR+)+0.152 for the unbuffered run and log (kΔks)=−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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