Synthesis of a Three-Bladed Propeller-Shaped Triple [5]Helicene

被引：50

作者：

Saito, Hiromu ^{[1
]}

Uchida, Akira ^{[1
]}

Watanabe, Soichiro ^{[1
,2
]}

机构：

[1] Toho Univ, Fac Sci, Dept Biomol Sci, Miyama 2-2-1, Funabashi, Chiba 2748510, Japan

[2] Toho Univ, Res Ctr Mat Integrated Properties, Miyama 2-2-1, Funabashi, Chiba 2748510, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 11期

关键词：

DOUBLE HELICENE; RACEMIZATION BARRIERS; PI-SYSTEMS; PHOTOCYCLIZATION; PHOTOCHEMISTRY; HEXABENZOTRIPHENYLENE; DERIVATIVES;

D O I：

10.1021/acs.joc.7b00486

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three-bladed propeller-shaped triple [5]-helicene was synthesized using eliminative and oxidative photocyclization reactions, which proceeded in 37 and 63% yields, respectively. Chromatographic purification gave a Mixture of diastereomers; and the PPM and PMM isomers were gradually converted to the thermodynamically more stable PPP and MAIM isomers at room temperature. The activation parameters for the racemization of the PPP and MMM isomers were determihed, and the structure of the triple [5]helicene was determined by X-ray crystallographic analysis.

引用

页码：5663 / 5668

页数：6

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