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The Novel Adamantane Isomer Tricyclo[4.4.0.03,9]decane (2-Homotwistbrendane)

✍ Scribed by Hans-Ruedi Känel; Camille Ganter

Publisher
John Wiley and Sons
Year
1985
Tongue
German
Weight
628 KB
Volume
68
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

Two synthetic approaches to the novel C~10~H~16~ hydrocarbon tricyclo[4.4.0.0^3,9^]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[4.3.0.0^3,8^]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 C~1~ 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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