[123]Tetramantane: Parent of a New Family of σ-Helicenes

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• 作者：Peter R. Schreiner ; Andrey A. Fokin ; Hans Peter Reisenauer ; Boryslav A. Tkachenko ; Elemr Vass ; Marilyn M. Olmstead ; Dieter Blser ; Roland Boese ; Jeremy E. P. Dahl ; Robert M. K. Carlson
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：August 19, 2009
• 年：2009
• 卷：131
• 期：32
• 页码：11292-11293
• 全文大小：141K
• 年卷期：v.131,no.32(August 19, 2009)
• ISSN：1520-5126

文摘

We present a new type of σ-helical structure based on a diamondoid (nanodiamond) framework, C₂-symmetric [123]tetramantane, whose (+) and (−) isomers could be enantioseparated by HPLC techniques. Bromination of the enantiopure hydrocarbon led to the isolation of (+)-7-bromo-[123]tetramantane, which could be crystallized and subjected to X-ray structure analysis. Using the anomalous dispersion, we have identified this compound as the P isomer for the hydrocarbon moiety. Experimental and computed optical rotatory dispersion (ORD) and vibrational circular dichroism (VCD) spectra independently and in agreement with the X-ray structure analysis gave M-(−) as the configuration of the second eluted parent hydrocarbon isomer.