An Efficient Synthesis of Functionalized Helicenes

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• 作者：Thomas J. Katz ; Longbin Liu ; Nikolaos D. Willmore ; Joseph M. Fox ; Arnold L. Rheingold ; Shuhao Shi ; Colin Nuckolls ; and Barry H. Rickman
• 刊名：Journal of the American Chemical Society
• 出版年：1997
• 出版时间：October 22, 1997
• 年：1997
• 卷：119
• 期：42
• 页码：10054 - 10063
• 全文大小：473K
• 年卷期：v.119,no.42(October 22, 1997)
• ISSN：1520-5126

文摘

[5]- and [6]helicenebisquinones can be preparedeasily and in quantity by combining enol ethers of 1,4-diacetylbenzene or 2,7-diacetylnaphthalene withp-benzoquinone. Similar diethenyl aromatics that eitherhave noether functions or have them attached not to the double bonds, but tothe aromatic rings, give the correspondinghelicenes in only low yields and low purities.[6]Helicenebisquinone 11c is resolved into itsenantiomers. An X-raydiffraction analysis of the adduct of one of these enantiomers andL-prolinol shows the absolute stereochemistryof11c and the regiochemistry with which the amine adds to thequinone.