The solvolytic behaviour of exo- and endo-bicyclo[3,2,1]octane-6-toluene-p-sulphonates
作者:R. A. Appleton、J. C. Fairlie、R. McCrindle、W. Parker
DOI:10.1039/j39680001716
日期:——
The buffered acetolysis of exo-bicyclo[3,2,1]octane-6-toluene-p-sulphonate (12; R = OTs) has been found to give exo-2-bicyclo[3,2,1]octyl acetate, 40%(16; R = OAc), 2-bicyclo[2,2,2]octyl acetate, 44%(17; R = OAc), and exo-6-bicyclo[3,2,1]octyl acetate, 16%(12; R = OAc), whereas the corresponding endo-6-isomer (13; R = OTs) gave (16; R = OAc), 19%, (17; R = OAc), 21%, and (12; R = OAc), 60%. The significance
的缓冲乙酰解外-双环[3,2,1]辛烷-6-甲苯p -磺酸盐(12; R = OTS)已经发现,得到外-2-二环[3,2,1]辛基,乙酸40%(16; R = OAc),乙酸2-双环[2,2,2]辛酯,44%(17; R = OAc),和exo -6-双环[3,2,1]乙酸辛酯,16 %(12; R = OAc),而相应的内在-6异构体(13; R = OTs)给出(16; R = OAc),19%,(17; R = OAc),21%和(12 ; R = OAc),60%。根据迄今未观察到的双环[3,2,1]中的4,6-氢化物位移,讨论了这些结果以及通过类似处理三环[3,2,1,0 2,7 ]辛烷获得的结果的重要性。辛烷骨架。