Cyclic Polyolefins. XXVI. Conversion of Cycloöctatetraenyl Phenyl Ketone to an Acyclic Tetraene<sup>*</sup>
作者:Arthur C. Cope、David J. Marshall
DOI:10.1021/ja01109a048
日期:1953.7
Abstract : Cyclooctatetraenyllithium was converted to bicyclooctatetraenyl by coupling in the presence of CoClsub2, and to cyclooctatetraenyl phenyl ketone (I)(mp = 38 deg to 39.5 deg C) by reaction with benzonitrile followed by hydrolysis of the intermediate imine. The ketone I formed a 1:1 complex with AgNOsub3 and a 2, 4-dinitrophenylhydrazone. Hydrogenation of I yielded benzycyclooctane and 1-cyclooctenyl
摘要 : 环辛四烯基锂在 CoClsub2 存在下通过偶联转化为双环辛四烯基,并通过与苯甲腈反应,然后水解中间体亚胺,转化为环辛四烯基苯基酮 (I)(mp = 38 摄氏度至 39.5 摄氏度)。酮 I 与 AgNOsub3 和 2, 4-二硝基苯腙形成 1:1 复合物。I的氢化产生苄环辛烷和1-环辛烯基苯基酮(II);用 LiAlHsub4 还原形成环辛四烯基苯基-羰基,其特征在于 2.78 和 2.93 微米的红外光谱带。在与 PhMgBr 反应时,我进行了开环并产生了无环酮 1, 9-diphenylnona-2, 4, 6, 8-tetraen-1-one (III)(mp = 125 摄氏度至 126.2 摄氏度),它对大气中的 O. III 与由 7-苯基-七-2、4、6-三烯醛和苯乙酮制备的样品相同。III yeidled 1, 9-diphenylnonan-1-one 的氢化。PhMgBr