NEW HETEROAROMATIC COMPOUNDS .1. 9-AZA-10-BORA-PHENANTHRENE
NEW HETEROAROMATIC COMPOUNDS .1. 9-AZA-10-BORA-PHENANTHRENE
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DOI：
10.1039/jr9580003073
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发表时间：
1958-01-01
期刊：
影响因子：
--
通讯作者：
PETTIT, R
中科院分区：
文献类型：
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作者：
DEWAR, MJS;KUBBA, VP;PETTIT, R
芳烃中的一个碳原子被氮取代，产生等共轭正离子；例如，吡啶离子以这种方式与苯相连。用硼代替会得到类似的负离子。一对碳原子，一个被氮原子取代，一个被硼原子取代，就会得到一个中性的芳香体系。硼唑是迄今为止唯一已知的这种化合物；我们现在描述一个类似的菲的类似物，用9:10碳原子取代。制备了母体化合物以及与硼相连的氯、羟基、甲基、乙基和苯基衍生物；它们具有预期的芳香性。如果芳烃中的一个碳原子被氮取代，则得到一个等共轭正离子；例如，吡啶离子C5NH6+以这种方式与苯C6H6相连。用硼取代一个碳原子同样会产生等共轭负离子，如C， BH6-，但目前还没有这种类型的化合物。由此可见，一对碳原子，一个被氮原子取代，一个被硼原子取代，会产生中性芳香体系；因此三种这样的分子(I)、（11）和（111）应该能够存在，它们都与苯同偶联。人们早就认识到，硼唑（IV）就是这种类型的，它是由苯中所有三对碳原子被取代而衍生出来的；硼唑的化学性质和光谱性质表明它是芳香的。然而，目前还没有其他芳香硼化合物被制备出来（除非氮化硼被认为是石墨的类似物），因此我们对这类新的芳香体系进行了一般性的研究。本文介绍了用氮取代9碳原子和用硼取代10碳原子从菲衍生的化合物的制备及其性质。
Replacement of one carbon atom in an aromatic hydrocarbon by nitrogen gives rise to an isoconjugate positive ion; eg, the pyridinium ion is related in this way to benzene. Replacement by boron should give an analogous negative ion. Replacement of a pair of carbon atoms, one by nitrogen and one by boron, should therefore give a neutral aromatic system. Borazole is the only hitherto known compound of this type; we now describe a similar analogue of phenanthrene with the 9: 10-carbon atoms so replaced. The parent compound, and derivatives with chlorine, hydroxy, methyl, ethyl, and phenyl attached to boron, have been prepared; they have the expected aromatic properties.IF one carbon atom in an aromatic hydrocarbon is replaced by nitrogen, an isoconjugate positive ion is obtained; for example, the pyridinium ion C5NH6+ is related in this way to benzene, C6H6. Replacement of one carbon atom by boron should likewise give rise to an isoconjugate negative ion, eg, C, BH6-, but no compounds of this type are known. It follows that replacement of a pair of carbon atoms, one by nitrogen and one by boron, should give rise to a neutral aromatic system; thus three such molecules (I),(11), and (111) should be capable of existence, all isoconjugate with benzene. It has long been recognised that borazole (IV) is of this type, being derived from benzene by replacement of all three pairs of carbon atoms; the chemical and spectroscopic properties of borazole indicate that it is aromatic. However, no other such aromatic boron compounds have yet been prepared (unless boron nitride is regarded as such an analogue of graphite), and we have therefore undertaken a general study of this new class of aromatic system. In this preliminary paper we describe the preparation and properties of compounds derived from phenanthrene by replacing the 9-carbon atom by nitrogen and the 10-carbon atom by boron.