
TY  - JOUR
A1  - Della, EW 
A1  - Knill, AM 
T1  - Synthesis of Bridgehead Substituted Bicyclo[2.2.1]Heptanes. Radical Cyclization of an Oxime Ether and an &#945;,&#946;-Unsaturated Ester
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1994
VL  - 47
IS  - 10
SP  - 1833
EP  - 1841
KW  - 
UR  - https://doi.org/10.1071/CH9941833 
N2  - The synthesis of bicyclo[2.2.1]heptanes with useful functionality at each bridgehead is achieved by radical cyclization of appropriately substituted 4-methylene- and 4-benzyloxyimino- cyclohexylmethyl radicals. The latter process, for example, leads to a bridgehead amine. Optimum yields are achieved when the reactions are conducted at 110° with slow addition of tributyltin hydride; under these conditions, the uncyclized isomer is either not detected, or formed in very small quantity. Production of a mixture of five- and six-membered cycloalkanones from similar treatment of the analogous 4-oxocyclohexylmethyl radicals reveals that the reaction is medicated by the corresponding 1-norbornyloxy radical. 
ER  -

