
%0 Journal Article
%A Cable, J 
%A Macleod, JK 
%T The synthesis of specifically deuterated analogues of Bicyclo[3,3,1]nonan-3-one
%J Australian Journal of Chemistry
%D 1973/10/01
%V 26
%N 10
%P 2147-2152
%K 
%R https://doi.org/10.1071/CH9732147
%U https://www.publish.csiro.au/paper/CH9732147 
%X endo-Bicyclo[3,3,1]nonan-3-ol (1), bicyclo[3,3,1]nonan-3-one (2), and a number of specifically deuterated analogues of these compounds have been synthesized from bicyclo[3,3,1]nonane-3,7-dione (3) by the following procedure.     Reduction of (3) with sodium borohydride gave 1-hydroxy-2- oxaadamantane (4) which was converted into 7-bromobicyclo[3,3,1]nonan- 3-one (6) on treatment with hydrobromic acid. Triphenyltin hydride was used to achieve replacement of the bromine atom by a hydrogen atom to give bicyclo[3,3,1]nonan-3-one (2).     Substitution of sodium borohydride by sodium borodeuteride gave endo-7-deuterobicyclo[3,3,1]nonan-3-one (2b) whereas the use of triphenyltin deuteride in place of triphenyltin hydride led to exo-7- deuterobicyclo[3,3,1]nonan-3-one (2a). The scheme also provided access to the [7-D2], [6,8-D4], and [6,7,8-D6] bicyclo[3,3,1]nonan-3-ones. 
