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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

RD Allan and RJ Wells

Australian Journal of Chemistry 23(8) 1625 - 1633
Published: 1970

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.

https://doi.org/10.1071/CH9701625

© CSIRO 1970

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