Issue 4, 1975

Acid-catalysed cyclisations of cyclo-octenylidene derivatives to produce bicyclo[3.3.1]nonanes

Abstract

Heating ethyl (cyclo-oct-4-enylidene)acetate (8) with boron trifluoride–ether complex in benzene gives a mixture of ethyl 1-phenylbicyclo[3.3.1]nonane-9-carboxylate (11) and the corresponding acid (12). Reduction of (11) with lithium aluminium hydride followed by dehydration yields 9-methylene-1-phenylbicyclo[3.3.1]nonane (14) whose structure was confirmed by an independent synthesis.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1975, 340-345

Acid-catalysed cyclisations of cyclo-octenylidene derivatives to produce bicyclo[3.3.1]nonanes

R. S. Atkinson and R. H. Green, J. Chem. Soc., Perkin Trans. 1, 1975, 340 DOI: 10.1039/P19750000340

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