
%0 Journal Article
%A Cambie, RC 
%A Palmer, BD 
%T Chemistry of the Podocarpaceae. LXI. The rearrangement of aryl phosphates to <I>ortho</I>-hydroxyaryl phosphonates
%J Australian Journal of Chemistry
%D 1982/04/01
%V 35
%N 4
%P 827-837
%K 
%R https://doi.org/10.1071/CH9820827
%U https://www.publish.csiro.au/paper/CH9820827 
%X Treatment of methyl 12-(diethoxyphosphoryloxy)podocarpa-8,11,13-trien-19-oate (14) or its 13-bromo derivative (7) with butyllithium effects a rearrangement of the phosphate group to give methyl 13-diethoxyphosphoryl-12-hydroxypodocarpa-8,11,13-trien-19-oate (11) in high yield. Similar treatment of some simple aryl phosphates indicates that the rearrangement is general. The reaction, which probably occurs by means of an ortho-metallation-nucleophilic displacement sequence, is superior to existing methods for the preparation of o-hydroxyaryl phosphonates. 
