58008-63-2Relevant academic research and scientific papers
Front Side Attack on the Bicyclopentane System by Halonium Ion; Halogenation of Dehydronoriceane
Katsushima, Takeo,Yamaguchi, Ryohei,Iemura, Satoshi,Kawanisi, Mituyosi
, p. 133 - 135 (1980)
Halogenation of dehydronoriceane (1) in dichloromethane in the dark exclusively or predominantly gave the trans-4,5-dihalogenoethanonoradamantanes (2) providing decisive evidence for front side attack on the bicyclopentane system by halonium ions; the reaction is susceptible to the solvent and halogen used.
Noriceane (Tetracyclo2,6.04,9>undecane) and 3,5-Dehydronoriceane (Pentacyclo2,6.03,5.04,9>undecane)
Katsuhima, Takeo,Yamaguchi, Ryohei,Kawanisi, Mituyosi
, p. 3245 - 3247 (2007/10/02)
Heating a mixture of endo, exo- and endo, endo-2,4-dibromohomoadamantanes at 180 deg C in hexamethylphosphoric triamide (HMPT) brings about a novel skeletal rearrangement with concomitant dehydrobromination to give tricyclo4,9>undeca-2,5-diene (5) in 88percent yield.Direct photoexcitation of 5 in diethyl ether induces an intramolecular cycloaddition to produce 3,5-dehydronoriceane (2).The bicyclopentane moiety constrained in the cage structure of 2 shows almost the same 13C-H coupling constants as those of bicyclopentane itself.Finally hydrogenation of 2 over PtO2 easily proceeds to afford noriceane, which is named after the structure of iceane.
