ORGN 516 |
Factors influencing the autoxidation of non-conjugated dienes
| Keri A. Tallman and Ned A. Porter. Department of Chemistry, Vanderbilt University, Nashville, TN 37235 |
The autoxidation of non-conjugated dienes (1), such as methyl linoleate, is mediated by free radical chain reactions. When oxidations are carried out in the presence of high concentrations of α-tocopherol, only the kinetic products are formed (4 and 5). The product distribution is dependent on the partitioning of O2 (α) across the pentadienyl radical (2), as well as the rearrangement (kβ) of the bis-allylic peroxyl radical (3). We have shown that the diene olefin geometry significantly affects these reactions. In addition, the diene substituent (R) plays a major role in determining the outcome of the product distribution. The factors that influence the autoxidation of non-conjugated dienes will be presented. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Sci-Mix
Division of Organic Chemistry
The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004
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