作者:E. Alexander Hill、Young-Whan Park
DOI:10.1016/0022-328x(88)80667-3
日期:1988.11
30dimethylmethylenecyclopropane were prepared and hydroborated using various borane reagents. Changes in the borane solutions as a result of heating were studied by NMR and by oxidation to alcoholds. Ring-cleavage rearrangement reactions were observed, analogous to rearrangements previously found for cyclopropylmethyl Grignard reagents and for unsubstituted cyclopropylmethylboranes Methyl substitution slows the
制备2,2,3-三甲基-和2,30二甲基亚甲基环丙烷,并使用各种硼烷试剂进行氢硼化。通过NMR和氧化成醇类研究了加热导致的硼烷溶液的变化。观察到环裂解的重排反应,类似于先前发现的对于环丙基甲基格氏试剂和未取代的环丙基甲基硼烷的重排。甲基取代减慢了涉及键与被取代的环碳的裂解的重排,并且当与金属甲基顺式时具有特别大的作用。在2,2,3-三甲基环丙基甲基系统中,环裂解重排不会完全完成,而是达到了一个平衡,在该平衡中,大量的反式异构体仍然存在。在2,3-二甲基环丙基甲基系统中发生重排,同时保留了硼迁移到的环碳上的构型。本工作的结果表明双环丁烷的碳硼化的机械重新解释。