
%0 Journal Article
%A Clark-Lewis, JW 
%A McGarry, EJ 
%T Hydroboration of Flav-3-enes, and oxidation to 2,4-<I>trans</I>-Flavan-4-ols, 2,3-<I>trans</I>-Flavan-3-ols, and 1,3-Diarylpropane derivatives
%J Australian Journal of Chemistry
%D 1973/04/01
%V 26
%N 4
%P 809-818
%K 
%R https://doi.org/10.1071/CH9730809
%U https://www.publish.csiro.au/paper/CH9730809 
%X Hydroboration of flav-3-enes has been found to be sensitive to electron release from substituents in the A-ring. Flav-3-enes which lack electron-releasing substituents in the A-ring give 2,4-trans-flavan-4- ols as the principal non-phenolic products. Electron-releasing substituents in the A-ring favour boration at the 3-position, and the boranes so formed suffer ring fission, which leads to the isolation of phenolic 1,3-diarylpropane derivatives as well as 2,3-trans-flavan-3- ols. Ring fission of the intermediate borane is minimized by reducing the temperature of hydroboration. N.m.r. data are presented on the compounds obtained. 
