Solvolysis of trans-1-methylbicyclo[4,4,0]dec-4-yl toluene-p-sulphonates

Abstract

trans-cis- and trans-trans-1-Methylbicyclo[4,4,0]dec-4-yl toluene-p-sulphonates have been prepared and rates of solvolysis measured in acetic acid and formic acid; a detailed analysis has been made of the products of acetolysis. Rates of formolysis of trans-cis- and trans-trans-bicyclo[4,4,0]dec-4-yl toluene-p-sulphonates have also been determined. The substitution of a methyl group into the 1-position the decalyl system has been shown to have little effect on the solvolysis of the equatorial derivatives but produces some rate enhancement of the axial toluene-p-sulphonates. This effect is discussed in terms of hydrogen participation and the decrease of a non-bonded interaction between the methyl group and 3-axial hydrogen.