
TY  - JOUR
A1  - Cable, J 
A1  - Macleod, JK 
T1  - The synthesis of specifically deuterated analogues of Bicyclo[3,3,1]nonan-3-one
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1973
VL  - 26
IS  - 10
SP  - 2147
EP  - 2152
KW  - 
UR  - https://doi.org/10.1071/CH9732147 
N2  - 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. 
ER  -

