The adamantane rearrangement of 1,2-trimethylenenorbornanes. Part IV. Hydride-ion abstraction in 1,2-exo-trimethylenenorbornane
作者:Alfred Michael Klester、Camille Ganter
DOI:10.1002/hlca.19850680113
日期:1985.2.13
In the AlBr3-catalyzed adamantane rearrangement in CS2 of 1,2-exo-trimethylenenorbornane (1) to 2-endo,6-endo-trimethylenenorbornane (3), hydride-ion abstraction occurs at C(6) from the exo-side. The kH/kD value for competition between 1 and 5 (Dexo-C(6)) was 1.58 ± 0.05, whereas no kinetic isotope effect was operative for competition between unlabeled 1 and 4 (Dendo-C(5)) and between 1 and 6 (Dendo-C(6))
在AlBr 3催化的金刚烷重排中,CS 2从1,2-外-三亚甲基降冰片烷(1)还原为2-内,6-内-三亚甲基降冰片烷(3),氢化物离子在C(6)上从外-发生。边。在1和5之间竞争的k H / k D值(D exo -C(6))为1.58±0.05,而对于未标记1和4之间的竞争则没有动力学同位素效应(D endo -C(5))。和1之间和6(D内-C(6))。