
%0 Journal Article
%A Eastwood, FW 
%A Mifsud, RD 
%A Perlmutter, P 
%T Acyclic Stereocontrol of Free Radical Reactions Involving Alkyl 2-(1-Hydroxyalkyl)propenoates
%J Australian Journal of Chemistry
%D 1994/12/01
%V 47
%N 12
%P 2187-2200
%K 
%R https://doi.org/10.1071/CH9942187
%U https://www.publish.csiro.au/paper/CH9942187 
%X The addition of cyclohexyl and t-butyl free radicals to silylated derivatives of alkyl 2-(1-hydroxyalkyl) propenoates was found to be stereoselective . In the case of the cyclohexyl radical the stereoselectivity was dependent upon the conditions used to generate the free radical and to quench the intermediate. Stereoselectivity in additions of the t-butyl radical was found to be temperature-dependent. In all cases stereoselectivity increased as the steric bulk of the group attached to the carbinol oxygen increased. A simple model which accounts for the stereoselectivity is proposed. 
