Deuterium isotope effects in the solvolytic reactivity of simple alkylvinyl trifluoromethanesulphonates

Abstract

The kinetic as well as product deuterium isotope effects have been measured in the solvolysis of 1-trideuteriomethyl-2-methylprop-1-enyl (2b), cis-(3b), and trans-2-deuterio-1-methylprop-1-enyl (4b) trifluoromethanesulphonates as well as the 3,3,3-trideuterio-1-methyl-2-trideuteriomethylprop-1-enyl ester (2c). At 75° in aqueous 60% ethanol for (2b)k_H/k_D= 1·54, for (3b) 1·25, for (4b) 2·01, and for (2c) 0·96. The significance of these results are discussed.