19270-13-4Relevant academic research and scientific papers
Secondary α hydrogen-deuterium kinetic isotope effects in the syn-elimination reaction of 2-phenylethyldimethylamine oxide
Smith, Peter James,Westaway, Kenneth Charles
, p. 2149 - 2153 (2007/10/02)
The secondary α-deuterium kinetic isotope effect has been measured for the thermal reaction of 2-phenylethyldimethylamine oxide in 90 mol percent DMSO-H2O at 60.0 deg C.A large secondary α-deuterium isotope effect of 1.158 per α-D was found, which indicates significant C-N bond rupture and very little double bond formation at the transition state for this concerted syn-elimination process.The observed large normal value for (kH/kD)α is discussed in terms of the use of secondary α-D isotope effects for the determination of stereochemistry for a concerted elimination process.Various isotope effects found for the syn elimination of the above amine oxide and those for the anti elimination of 2-arylethyltrimethylammonium salts with ethoxide are considered with respect to the relative transition state structures for syn- and anti-elimination reactions.
