38787-96-1Relevant articles and documents
MECHANISM OF THE OZONOLYSIS OF PROPENE IN THE LIQUID PHASE.
Choe,Srinivasan,Kuczkowski
, p. 4703 - 4704 (2007/10/02)
Propylene was ozonized in isobutane, hlorodifluoromethane, and methyl chloride solvents. Propylene ozonide, ethylene ozonide, and 2-butene ozonide (cis and trans isomers) were obtained in ratios of about 82:16:2. The amount of butene ozonide increased while that of ethylene ozonide usually decreased for reactions in the presence of added acetaldehyde. The cis-trans stereochemistry of the butene cross ozonide from propylene was studied at various conditions. Usually the cis isomer was preferentially formed, but addition of acetaldehyde could alter this. The cis-(trans-butene ozonide ratio was 67/33 when formed from cis- or trans-2-butene in CHClF//2 and 50/50 as a cross ozonide from trans-2-pentene. The kinetic secondary isotope effects upon ozonolysis of propene-2-d//1 (k//H/k//D equals 0. 88 (6) and propene-1-d//1 (0. 88 (8) were evaluated. These results are discussed with reference to the Criege mechanism of ozonolysis. 37 refs.
Infrared Spectra and Photochemistry of the Primary and Secondary Ozonides of Propene, trans-2-Butene, and Methylpropene in Solid Argon
Andrews, Lester,Kohlmiller, Christopher K.
, p. 4548 - 4557 (2007/10/02)
Reactions of propene, trans-2-butene, and methylpropene with 16O3, 16,18O3,and 18O3 have been studied in solid xenon at 80 - 100 K and CF3Cl solution at 130 - 150 K.The major reaction product in solution was identified as the secondary ozonide (SOZ) from the matrix infrared spectrum.Reaction products in solid xenon for propene and trans-2-butene were SOZ, primary ozonide (POZ), and aldehyde, and for methyl propene the products were POZ, oxide, and acetone.The POZ's were characterized by an intense antisymmetric O-O-O stretching mode at 640 - 700 cm-1.Photolysis of the propene and 2-butene SOZ's gave formic acetic anhydride, hydroxy ester, and acid-aldehyde dimer decomposition products.
The Mechanism of Ozone-Alkene Reactions in the Gas Phase. A Mass Spectrometric Study of the Reactions of Eight Linear and Branched-Chain Alkenes
Martinez, Richard I.,Herron, John T.,Huie, Robert E.
, p. 3807 - 3820 (2007/10/02)
The stable products of the low-pressure (4 - 8 torr (1 torr = 133.33 Pa)) gas-phase reactions of ozone with ethene, propene, 2-methylpropene, cis-2-butene, trans-2-butene, trans-2-pentene, 2,3-dimethyl-2-butene, and 2-ethyl-1-butene have been identified by using a photoionization mass spectrometer coupled to a stirred-flow reactor.The products observed are characteristic of (i) a primary Criegee split to an oxoalkane (aldehyde or ketone) and a Criegee intermediate, (ii) reactions of the Criegee intermediates such as unimolecular decomposition, secondary ozonide formation, etc., and (iii) secondary alkene chemistry involving OH and other free-radical products formed by the unimolecular decomposition of the Criegee intermediates.The secondary OH - alkene - O2 reactions account for a significant fraction of the alkene (CnH2n) consumed and lead to characteristic products such as Cn dioxoalkanes nH2n + 30)>, Cn acyloins nH2n + 32)>, and Cn alkanediols nH2n + 34)>.Cn oxoalkanes and Cn epoxyalkanes observed at m/e (CnH2n + 16) are probably formed primarily via epoxidation of the alkene by O3.A general mechanism has been proposed to account for the observations.
