Factors influencing the competitive rates of free-radical addition of ethyl 2-bromocarboxylates to selected alkene pairs Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/gf06g523z

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  • A study of the effects of structural modification at the alpha position of ethyl 2-bromocarboxylates on their rates of addition to two alkene pairs was undertaken. In the competition between 3-propoxypropene and 1-octene at 70°, a 37% increase in selectivity was observed in going from carboxylates generating primary radicals to those generating tertiary radicals. These results yield good correlations with electronic and/or steric parameters. When the competition between 1-methylcyclohexene and 1-octene was examined, no simple systematic variation of selectivity with structure was observed. An explanation is offered, which is based on the greater persistence of hindered carboethoxyalkyl radicals and the resultant changes in transition state structure.
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