77419-07-9Relevant academic research and scientific papers
Silver(I) Ion-catalyzed Rearrangement of 3,5-Dehydronoriceane (Pentracyclo2,6.03,5.04,9>undecane). Empirical Force-field Calculations and Behavior of 3-Noricyl(Tetra2,6.04,9>undec-3-yl) Cation
Katsushima, Takeo,Yamaguchi, Ryohei,Kawanisi, Mituyosi,Osawa, Eiji
, p. 3313 - 3317 (2007/10/02)
Treatment of 3,5-dehydronoriceane (1) with a catalytic amount of silver tetrafluoroborate results in a novel skeletal rearrangement to afford tetracyclo2,6.03,9>undec-4-ene(2,4-ethenonoradamantane)(5) in 85 percent yield.Empirical force-field calculations suggest that there is no substantial difference in strain energies between 1 and bicyclopentane which is inert toward silver(I) ion.Acetolysis of endo-3-noricyl(endo-tetracyclo2,6.04,9>undec-3-yl) tosylate (7) gives exo-3-acetoxynoriceane(exo-3-acetoxytetracyclo2,6.04,9)undecane (11), exo- 4-acetoxytetracyclo2,6.03,9>undecane (12), and 5 in a ratio of 36 :42 :22.Similar acetolysis of exo-isomer of 7 gives the same products but in different ratio (11:12:5=9:47:44).A stepwise carbocation mechanism is proposed for the above mentioned silver(I) ion-catalyzed rearrangement.
