Stopped-Flow Studies of the Mechanisms of Ozone-Alkene Reactions in the Gas Phase: Tetramethylethylene

Article abstract of DOI:10.1021/j100288a036

The reaction of ozone with tetramethylethylene (TME) has been studied in the gas phase at 294 K and 530 Pa (4 Torr) with a stopped-flow reactor coupled to a photoionization mass spectrometer.The concentration of reactants and products were determined as a function of reaction time.The major products were (CH3)2CO, H2CO, CH3C(O)CH2OH (hydroxyacetone), and CH3C(O)C(O)H (methylglyoxal).Computer simulations of the experimentally observed temporal profiles supports the mechanism shown in the Scheme I.The "hot" ester channel R'C(O)OR''^* -> products> available to the H2COO formed by ozonolysis of terminal olefins R'R''C=CH2 is not available for alkyl substituted R'R''COO.Thus the secondary chemistry for R'R''COO is substantially different from that for H2COO.