DIASTEREOISOMERIZATION AND X-RAY CRYSTAL-STRUCTURE OF MESO-DI-(2H-CHROMENE-2-YL) ETHER

LONCAR, L and MINTAS, M and HERGOLDBRUNDIC, A and NAGL, A and TROTSCH, T and MANNSCHRECK, A (1995) DIASTEREOISOMERIZATION AND X-RAY CRYSTAL-STRUCTURE OF MESO-DI-(2H-CHROMENE-2-YL) ETHER. CROATICA CHEMICA ACTA, 68 (1). pp. 233-240. ISSN 0011-1643,

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Abstract

It was shown by X-ray crystal structure analysis that di-(2H-chromene-2-yl)-ether (1) exists in the meso-form, i.e. as (2S, 2'R)-1. The Xray structural data indicate, also, that geometries of the two 2H-1-benzopyran parts, of which the skeleton of 1 consists, are not identical, that is the molecule is pseudosymmetrical. The meso-1 undergoes thermally induced electrocyclic ring opening and reclosure. Thus, meso-1 equilibrates with enantiomers (2S, 2'S)-1 and (2R, 2'R)-1, as confirmed by their H-1-NMR spectra after preparative separation of stereoisomers using liquid chromatography on triacetylcellulose.

Item Type: Article
Uncontrolled Keywords: RACEMIZATION; ENANTIOMERS;
Depositing User: Dr. Gernot Deinzer
Last Modified: 19 Oct 2022 08:37
URI: https://pred.uni-regensburg.de/id/eprint/52618

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