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Unusual Rearrangement of the 4-Homoadamantyl Cation. One-step Preparation of 2, 6-Trimethylenebicyclo[2.2.2]octane

Homoadamantene is readily converted by Lewis-acid catalysa into a single major product 2- methyladamantane. 1 However, the behaviour of the 4-homoadamantyl cation generated from homoadamantene(1) and 4-homoadamantano1(2) by concentrated sulphuric acid in the presence of pentane was quite different! Instead of one, three major products (90-95% by glc) were formed in the ratio 2:l:l. Almost identical products distribution was obtained from both 1 and 2. 3 Two 1 minor components were identified as homoadamantane ($ and 2-methyladamantane (5) by H nmr. ir, and mass spectra, and glc comparison with authentic samples.

Lewis-acid catalysis ; 2-methyladamantane ; 4-homoadamantyl

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