Selective free radical reactions using supercritical carbon dioxide

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[1] Cormier, Philip J.
[2] Clarke, Ryan M.
[3] McFadden, Ryan M. L.
[4] Ghandi, Khashayar
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Ghandi, K. (kghandi@mta.ca) | 1600年 / American Chemical Society卷 / 136期
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We report herein a means to modify the reactivity of alkenes; and particularly to modify their selectivity toward reactions with nonpolar reactants (e.g; nonpolar free radicals) in supercritical carbon dioxide near the critical point. Rate constants for free radical addition of the light hydrogen isotope muonium to ethylene; vinylidene fluoride; and vinylidene chloride in supercritical carbon dioxide are compared over a range of pressures and temperatures. Near carbon dioxide's critical point; the addition to ethylene exhibits critical speeding up; while the halogenated analogues display critical slowing. This suggests that supercritical carbon dioxide as a solvent may be used to tune alkene chemistry in near-critical conditions. © 2014 American Chemical Society;
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