The first enantiomerically pure triangulane (M)-trispiro[2.0.0.2.1.1]nonane is a sigma-[4]helicene - Research portal of Justus Liebig University Giessen:

Journal article

The first enantiomerically pure triangulane (M)-trispiro[2.0.0.2.1.1]nonane is a sigma-[4]helicene

Authors list: de Meijere, A; Khlebnikov, AE; Kostikov, RR; Kozhushkov, SI; Schreiner, PR; Wittkopp, A; Yufit, DS

Publication year: 1999

Pages: 3474-3477

Journal: Angewandte Chemie International Edition

Volume number: 38

Issue number: 23

ISSN: 1433-7851

DOI Link: https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3474::AID-ANIE3474>3.0.CO;2-6

Publisher: Wiley

Abstract:

A remarkably high specific rotation, even at 589 nm, is shown by (M)‐1, the first enantiomerically pure unbranched [4]triangulane, although it has no chromophore that would lead to any significant absorption above 200 nm. This outstanding rotatory power is in line with a helical arrangement of its σ bonds, as confirmed by high‐level computations. Thus, it is appropriate to call (M)‐1 a “σ‐[4]helicene”, the first σ‐bond analogue of the aromatic [n]helicenes.

Authors/Editors

- Uni.-Prof. Dr. Peter Richard Schreiner, PhD

Citation Styles

Harvard Citation style: de Meijere, A., Khlebnikov, A., Kostikov, R., Kozhushkov, S., Schreiner, P., Wittkopp, A., et al. (1999) The first enantiomerically pure triangulane (M)-trispiro[2.0.0.2.1.1]nonane is a sigma-[4]helicene, Angewandte Chemie International Edition, 38(23), pp. 3474-3477. https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3474::AID-ANIE3474>3.0.CO;2-6

APA Citation style: de Meijere, A., Khlebnikov, A., Kostikov, R., Kozhushkov, S., Schreiner, P., Wittkopp, A., & Yufit, D. (1999). The first enantiomerically pure triangulane (M)-trispiro[2.0.0.2.1.1]nonane is a sigma-[4]helicene. Angewandte Chemie International Edition. 38(23), 3474-3477. https://doi.org/10.1002/(SICI)1521-3773(19991203)38:23<3474::AID-ANIE3474>3.0.CO;2-6