The Novel Adamantane Isomer Tricyclo[4.4.0.03,9]decane (2-Homotwistbrendane) |
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Authors: | Hans-Ruedi K nel,Camille Ganter |
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Affiliation: | Hans-Ruedi Känel,Camille Ganter |
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Abstract: | Two synthetic approaches to the novel C10H16 hydrocarbon tricyclo[4.4.0.03,9]decane ( 1 ; 2-homotwistbrendane), one of the 19 members of the adamantaneland, and its Lewis-acid-catalyzed rearrangement are described. One route starts from tricyclo[4.3.0.03,8]nonan-2-one ( 2 ; 2-twistbrendanone). The missing tenth C-atom is introduced by ring enlargement (Tiffeneau-Demjanov method). Starting from methyl 8,9,10-trinorborn-5-ene-2-endo-carboxylate ( 8 ), ring enlargement by one C-atom, regio- and stereoselective introduction of a C1 unit to a 2-endo,6-endo-disubstituted bicyclo[3.2.1]octane, and ring closure by acyloin condensation are the key steps in the second approach. |
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