Canadian journal of chemistry

Secondary α hydrogen-deuterium kinetic isotope effects in the syn-elimination reaction of 2-phenylethyldimethylamine oxide

PJ Smith, KC Westaway

Index: Smith, Peter James; Westaway, Kenneth Charles Canadian Journal of Chemistry, 1987 , vol. 65, p. 2149 - 2153

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Citation Number: 5

Abstract

The secondary α-deuterium kinetic isotope effect has been measured for the thermal reaction of 2-phenylethyldimethylamine oxide in 90 mol% DMSO-H2O at 60.0° C. A large secondary α-deuterium isotope effect of 1.158 per α-D was found, which indicates significant bond rupture and very little double bond formation at the transition state for this concerted syn-elimination process. The observed large normal value for (k H/k D) α is discussed in ...