Synthesis of 2, 11-dehydrohomoadamantane (tetracyclo [5.3. 1.02, 4.03, 9] undecane) and 2, 11-dehydrohomoadamant-4-ene (tetracyclo [5.3. 1.02, 4.03, 9] undec-5- …

T Katsushima, K Maki, R Yamaguchi…

Index: Katsushima, Takeo; Maki, Ken'ichiro; Yamaguchi, Ryohei; Kawanisi, Mituyosi Bulletin of the Chemical Society of Japan, 1980 , vol. 53, # 7 p. 2031 - 2035

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Citation Number: 5

Abstract

Bromination of tricyclo [5.3. 1.0 4, 9] undeca-2, 5-diene gave endo-2, endo-6-and endo-2, exo-6-dibromotetracyclo [5.3. 1.0 3, 5. 0 4, 9] undecanes along with syn-11, endo-2- dibromotricyclo [4.3. 1.1 3, 8] undec-4-ene (10a) in a ratio of 3: 3: 1. A thermal treatment of the mixture of these dibromides at 140–150° C induced a skeletal rearrangement to afford 10a and syn-11, exo-2-dibromotricyclo [4.3. 1.1 3, 8] undec-4-ene (10b) in 87% yield (10a: ...