Some highly phenylated aliphatic nitro compounds
Some highly phenylated aliphatic nitro compounds
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DOI：
10.1021/ja01365a046
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发表时间：
1930-01-01
影响因子：
15
通讯作者：
Stone, JF
中科院分区：
文献类型：
--
作者：
Kohler, EP;Stone, JF
虽然脂肪族硝基化合物已成为许多优秀研究的主题，但它们仍然存在许多理论上的问题。人们对影响酸性形式稳定性的因素以及这些形式转化为真正的硝基化合物的方式、硝基和异硝基通过与烯键缀合而修饰的程度、硝基和异硝基的紧密结构知之甚少。硝基。由于简单硝基化合物的酸式寿命短，我们研究了一些苯基化的衍生物，期望饱和的代表物比迄今所研究的简单化合物更易处理，而且不饱和成员与相应的苯基化羰基化合物之间的比较将是有益的。我们的起始原料是硝基苯乙烯和硝基二苯乙烯。由于它易于聚合，前者证明对我们的目的相对无用，但后者使我们能够制备和研究更高度苯基化的饱和和不饱和硝基化合物。它与苯基溴化镁的反应与相应的不饱和酮-苯甲醛脱氧安息香一样容易，并且与不饱和酮一样，它显然只形成1，4-加成产物
Although aliphatic nitro compounds have been the subject of many excellent investigations theystill present a number of problems of theoreti-cal interest. Little is known about the factors that influence the sta-bility of the aci forms and the manner in which these pass into true nitro compounds, the extent to which the nitro and iso-nitro groups are modified by conjugation with ethylenic linkages, the intimate structure of nitro and iso-nitro groups. Since the life of the aci forms ofsimple nitro com-pounds is short, we have studied a number of phenylated derivatives in the expectation that the saturated representatives would be more tractable than the simpler compounds which have been studied heretofore, and that a comparison between the unsaturated members and the correspondingly phenylated carbonyl compounds would be instructive. Our starting materials were nitro styrene and nitro stilbene. Owing to the ease with which it polymerizes, the former proved comparatively useless for our purpose, but the latter enabled us to prepare and study still more highly phenylated saturated and unsaturated nitro compounds. It reacts with phenyl magnesium bromide as readily as does the corre-sponding unsaturated ketone—benzaldesoxybenzoin—and like the un-saturated ketone it forms, apparently exclusively, a 1, 4-addition product