Issue 12, 2011

[6]Saddlequat: a [6]helquat captured on its racemization pathway

Abstract

A dicationic [6]helicene congener captured on the racemization pathway in its saddle-shaped geometry is introduced. Synthesis, structure, resolution, and dynamic properties of this chiral [6]saddlequat in-between and its highly stereocontrolled transformation into enantiopure [6]helquat are discussed and demonstrated. The dynamic aspects established by experiment and supported by detailed DFT-D calculations are presented visually in the form of a movie (electronic table-of-contents and electronic supplementary information). The title [6]saddlequat was found to be an isolable chiral species on the entirely chiral enantiomerization pathway of a [6]helquat that is discussed as an example of Mislow's “rubber glove” molecule.

Graphical abstract: [6]Saddlequat: a [6]helquat captured on its racemization pathway

Supplementary files

Article information

Article type
Edge Article
Submitted
14 Jul 2011
Accepted
08 Aug 2011
First published
08 Sep 2011
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2011,2, 2314-2320

[6]Saddlequat: a [6]helquat captured on its racemization pathway

L. Adriaenssens, L. Severa, D. Koval, I. Císařová, M. M. Belmonte, E. C. Escudero-Adán, P. Novotná, P. Sázelová, J. Vávra, R. Pohl, D. Šaman, M. Urbanová, V. Kašička and F. Teplý, Chem. Sci., 2011, 2, 2314 DOI: 10.1039/C1SC00468A

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