Journal article

Publication year: 2009

Pages: 11292-11293

Journal: Journal of the American Chemical Society

Volume number: 131

Issue number: 32

DOI Link: https://doi.org/10.1021/ja904527g

Publisher: American Chemical Society

Abstract: 

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.

Harvard Citation style: Schreiner, P., Fokin, A., Reisenauer, H., Tkachenko, B., Vass, E., Olmstead, M., et al. (2009) [123]Tetramantane: Parent of a New Family of σ-Helicenes, Journal of the American Chemical Society, 131(32), pp. 11292-11293. https://doi.org/10.1021/ja904527g

APA Citation style: Schreiner, P., Fokin, A., Reisenauer, H., Tkachenko, B., Vass, E., Olmstead, M., Bläser, D., Boese, R., Dahl, J., & Carlson, R. (2009). [123]Tetramantane: Parent of a New Family of σ-Helicenes. Journal of the American Chemical Society. 131(32), 11292-11293. https://doi.org/10.1021/ja904527g