Synthesis and chemistry of hexamethyl-trans-15,16-dihydropyrene
Synthesis and chemistry of hexamethyl-trans-15,16-dihydropyrene
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六甲基反式15,16-二氢芘的合成与化学
DOI：
10.1021/jo00985a001
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发表时间：
1972
影响因子：
3.6
通讯作者：
L. Hall
中科院分区：
文献类型：
--
作者：
H. B. Renfroe;J. Gurney;L. Hall
Boekelheide、Phillips、2和Miyasaka等合成了反式-15，16-二甲基-1，2和反式-1，16-二乙基二氢化芘3，对Hiickel芳香性理论进行了很有意义的验证。这些独特的分子（1，R= CH 3或C2 H5）带有取代基，这些取代基完全包含在由平面14-x电子外围产生的空腔内。这些分子的物理和化学性质为Hückel理论提供了强有力的支持，Hückel理论预测芳香环的（4±· 2）x电子在环平面的上方和下方形成甜甜圈状的云。这样的ax云的中心可能是空的空间，这些分子提供了一个特殊的机会来研究x电子系统中的取代基对x云的影响，反之亦然。
The syntheses of trans-15, 16-dimethyl-1 2 and trans-it, l 6-diethy ldihy dropyrene3 by Boekelheide, 2-8 Phil-lips, 2 and Miyasaka3constitute a very interesting test of the Hiickel theory of aromaticity. These unique molecules (1, R= CH3 or C2H5) bear substituents which are contained completely within the cavity generated by the planar 14-x-electron periphery. The physical and chemical properties of thesemolecules provide strong support for the Hückel theory, which predicts that (4±· 2) x electrons of an aromatic ring form a doughnut-shaped cloud above and below the plane of the ring. The center of such ax cloud then might be empty space, and these molecules present a special opportunity to examine the effect ofsubstituent groups within a x-electron system on the x cloud, and vice versa.