Empirical force field calculations predict that 2,4-ethanonoradamantane (1) and 2,8-ethanonoradamantane (2) should be the most stable tetracyclic C11H16 isomers and both should have comparable stability; experimentally, AlBr3 isomerisation yielded only (1) and (2)(also synthesised independently) but in a ratio of 97:3.
S. A. Godleski, P. v. R. Schleyer and E. Ōsawa, J. Chem. Soc., Chem. Commun., 1976, 38 DOI: 10.1039/C39760000038
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