Reduction of 2-phenyl- and 2-methyl-exo-3,4-dichlorobicyclo[3.2.1]oct-2-enes with lithium aluminium hydride (LAH) or tributyltin hydride (TBTH) gave endo-2-phenyl-3-chlorobicyclo[3.2.1]oct-3-ene, 2-phenyl-3-chlorobicyclo[3.2.1]oct-2-ene and their methyl analogues. The action of both reagents on 2-phenyl-exo-3, 4-dibromobicyclo[3.2.1]oct-2-ene similarly resulted in reductive monodebromination to give normal and allylically rearranged products. Additionally, further reduction occurred to give endo-2-phenylbicyclo[3.2.1]oct-3-ene and 2-phenylbicyclo[3.2.1]-oct-2-ene. In all cases, LAH gave mainly the allylic rearrangement product whereas TBTH gave mostly unrearranged product. The reason for these differences could have been due either to the intervention of allylic radicals in the TBTH reduction or to differences in nucleophilicity. The results also show that LAH is equally efficaceous as TBTH in the reduction of these allylic halides and equally selective in the reduction of the vinyl bromides. The stereochemistry of the allylic rearrangement was shown to be synfacial in that hydride replaced halide on the same face of the molecule.

中文翻译：

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双环[3.2.1]辛烯基卤化物与金属氢化物的反应

用氢化铝锂（LAH）或氢化三丁基锡（TBTH）还原2-苯基-和2-甲基-exo -3,4-二氯双环[3.2.1]辛-2-烯，得到内基-2-苯基-3-氯双环[3.2.1]辛-3-烯，2-苯基-3-氯双环[3.2.1]辛-2-烯及其甲基类似物。两种试剂对2-苯基动作外型-3，4- dibromobicyclo [3.2.1]辛-2-烯同样导致还原monodebromination得到正常和烯丙重排产物。此外，发生进一步减少给内-2-苯基双环[3.2.1]辛-3-烯和2-苯基双环[3.2.1]-辛-2-烯。在所有情况下，LAH主要产生烯丙基重排产物，而TBTH主要产生未重排产物。这些差异的原因可能是由于烯丙基自由基对TBTH降低的干预或亲核性的差异。结果还表明，在减少这些烯丙基卤化物方面，LAH与TBTH具有相同的功效，在减少乙烯基溴化物方面具有同等的选择性。烯丙基重排的立体化学被证明是共界面的，因为氢化物取代了分子同一面上的卤化物。