The decomposition of Bicyclo[3,3,1]nonan-9-ylidene

Abstract

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.