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Trifluoromethanesulfonic acid catalyzed rearrangement of 2-and 4-homoprotoadamantane to methyladamantanes and the existence of methylprotoadamantane route. …

N Takaishi, Y Inamoto, K Aigami…

文献索引:Takaishi,N. et al. Journal of Organic Chemistry, 1977 , vol. 42, # 12 p. 2041 - 2047

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被引用次数: 14

摘要

Brief treatment of 2-homoprotoadamantane (10) with trifluoromethanesulfonic acid gave 4- homoisotwistane (4), homoadamantane (7), and 2-methyladamantane (6), while similar treatment of 4-homoprotoadamantane (1 1) afforded 4, 6, I-methyladamantane (5), 2, 4- bishomobrendane (15), and endo-2, 8-trimethylene-cis-bicyclo [3.3. 0] oc-tane (14), but no trace of 7. The absence of 7 in the latter reaction mixture precludes the possibility of ...