29478-31-7Relevant academic research and scientific papers
Stereochemistry of Olefin and Fatty Acid Oxidation. Part 1. Autooxidation of Hexene and Hepta-2,5-diene Isomers
Frankel, Edwin N.,Garwood, Robert F.,Vinson, John R.,Weedon, Basil C. L.
, p. 2707 - 2714 (2007/10/02)
The stereochemistry of the autooxidation of hex-1-ene, cis- and trans-hex-2-ene, cis- and trans-hex-3-ene, and of the three geometrical isomers of hepta-2,5-diene, has been determined by the reduction of the hydroperoxides produced and analysis of the resulting allylic alcohols.The relative proportions of the isomeric hydroperoxides are explicable in termes of the conformation of the parent olefins which are capable of giving delocalised radicals on hydrogen abstraction.
Stereochemistry of Olefin and Fatty Acid Oxidation. Part 1. Photosensitised Oxidation of Hexene and Hepta-2,5-diene Isomers
Frankel, Edwin N.,Garwood, Robert F.,Vinson, John R.,Weedon, Basil C. L.
, p. 2715 - 2718 (2007/10/02)
The stereochemistry of the photosensitised oxidation of hex-1-ene, cis- and trans-hex-2-ene, cis- and trans-hex-3-ene, and of the three geometrical isomers of hepta-2,5-diene, has been investigated by the reduction or hydrogenation of the hydroperoxides produced and analysis of the resulting allylic or saturated alcohols.The isomeric distribution of hydroperoxides from hexene isomers is that expected from the concerted ene reaction of singlet oxygen with the parent olefin oriented so as to favor the cis, cyclic process.In contrast to autooxidation, photosensitised oxidation of hepta-2,5-diene isomers produces a mixture of conjugated (67-70percent) and nonconjugated (30-33percent) hydroperoxides.The conjugated products formed are explicable in terms of the conformations of the parent dienes which have the least steric interactions.
