1,2endo-Trimethylenenorbornane. A novel isomer of adamantane |
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Authors: | Franz Josef Jggi Camille Ganter |
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Institution: | Franz Josef Jäggi,Camille Ganter |
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Abstract: | An easy approach to the novel adamantane isomer 1,2endo-trimethylenenorbornane (2) is described. Starting from a mixture of pent-4-ynylcyclopentadienes 3 the tricyclic monosaturated key intermediate 5 was prepared by intramolecular cycloaddition (→ 4 ) and subsequent regioselective reduction of the C(5), C(6) double bond. The title hydrocarbon 2 was obtained from 5 upon stereoselective hydrogenation by diimide. In addition specifically deuteriated analogues of 2 were prepared applying dideuteriodiimide. Compound 2 rearranged to 2endo, 6endo-trimethylenenorbornane (4-homobrendane, 10 ) in sulfuric acid as well as with aluminium bromide in carbon disulfide. |
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