T. Katsushima, Ken'ichiro Maki, R. Yamaguchi
Jul 1, 1980
Citations
0
Influential Citations
3
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Bromination of tricyclo[5.3.1.04,9]undeca-2,5-diene gave endo-2,endo-6- and endo-2,exo-6-dibromotetracyclo[5.3.1.03,5.04,9]undecanes along with syn-11,endo-2-dibromotricyclo[4.3.1.13,8]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[4.3.1.13,8]undec-4-ene (10b) in 87% yield (10a:10b=2:5). The new “non-bridgehead” 2,11-dehydrohomoadamantane was obtained by the hydrogenation of 10a and 10b followed by Wurtz type reductive cyclization. The unsaturated analogue, 2,11-dehydrohomoadamant-4-ene was also synthesized from 10a and 10b by the similar cyclization reaction.