The solvolyses of esters of 1-hydroxymethylbicyclononane, 5-hydroxymethylmethylenecyclo-octane, and 1-methyl-5-hydroxymethylcyclo-octene are described, together with the deaminations of the corresponding amines. The occurrence of 1,3-hydride shifts is reported, and the implications of the results, as regards the π-route to bicyclic molecules, are discussed.
S. H. Graham and D. A. Jonas, J. Chem. Soc. C, 1969, 188 DOI: 10.1039/J39690000188
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