Synthesis of Polycyclic Arenes Composed of Four-, Five-, Six-, and Eight-Membered Rings via an Unexpected Four-Membered Ring Formation Reaction

被引：0

作者：

Hirota, Soshi ^{[1
,2
]}

Nakano, Sachiko ^{[1
]}

Sugiyama, Haruki ^{[1
,2
,3
]}

Segawa, Yasutomo ^{[1
,2
]}

机构：

[1] Inst Mol Sci, Okazaki 4448787, Japan

[2] Grad Univ Adv Studies, Okazaki 4448787, Japan

[3] Comprehens Res Org Sci & Soci, Neutron Ind Applicat Promot Ctr, Ibaraki 3191106, Japan

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 45期

关键词：

BIPHENYLENES; REARRANGEMENTS;

D O I：

10.1021/acs.orglett.3c03039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of polycyclic arenes composed of four-, five-, six-, and eight-membered rings via an unexpected four-membered ring formation reaction is reported. The carbonylation of an octalithiated tetraphenylene yielded a tricarbonylated arene containing a four-membered ring or a tetracarbonylated one, depending on the carbonyl reagents. The structures were determined by X-ray crystallography, and their electronic properties were examined by using absorption spectroscopy and cyclic voltammetry. The antiaromaticity of the four-, five-, and eight-membered rings of these compounds was studied by theoretical calculations.

引用

页码：8062 / 8066

页数：5

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