
%0 Journal Article
%A Della, EW 
%A Knill, AM 
%T Synthesis of Bridgehead Substituted Bicyclo[2.2.1]Heptanes. Radical Cyclization of an Oxime Ether and an &#945;,&#946;-Unsaturated Ester
%J Australian Journal of Chemistry
%D 1994/10/01
%V 47
%N 10
%P 1833-1841
%K 
%R https://doi.org/10.1071/CH9941833
%U https://www.publish.csiro.au/paper/CH9941833 
%X 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. 
