
%0 Journal Article
%A Allan, RD 
%A Wells, RJ 
%T The decomposition of Bicyclo[3,3,1]nonan-9-ylidene
%J Australian Journal of Chemistry
%D 1970/08/01
%V 23
%N 8
%P 1625-1633
%K 
%R https://doi.org/10.1071/CH9701625
%U https://www.publish.csiro.au/paper/CH9701625 
%X The intramolecular decomposition products of bicyclo[3,3,1]nonan-9-ylidene, generated by thermal decomposition of the sodium salt of bicyclo[3,3,1]nonan-9-one-tosylhydrazone, have been investigated in protic and aprotic solvents and also without solvent. When bicyclo[3,3,1]nonan-9-ylidene is generated in the presence of excess base in aprotic solvents product analysis indicates that 1,3 insertion is predominant with some carbene rearrangement. When a protic solvent is used the product composition indicates a predominantly cationic intermediate. Decomposition of the carbene in the presence of a limited amount of base, even under aprotic conditions, gives rise to products resulting from both cationic and carbenoid intermediates. 
