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Spontaneous Generation of Chirality in Simple Diaryl Ethers.

Journal article
Authors Anders Lennartson
Anna Hedström
Mikael Håkansson
Published in Chirality
Volume 27
Issue 7
Pages 425-9
ISSN 1520-636X
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 425-9
Language en
Links dx.doi.org/10.1002/chir.22460
Keywords CD-spectroscopy;
Subject categories Chemical Sciences, Organic Chemistry

Abstract

We studied the spontaneous formation of chiral crystals of four diaryl ethers, 3-phenoxybenzaldehyde, 1; 1,3-dimethyl-2-phenoxybenzene, 2; di(4-aminophenyl) ether, 3; and di(p-tolyl) ether, 4. Compounds 1, 3, and 4 form conformationally chiral molecules in the solid state, while the chirality of 2 arises from the formation of supramolecular helices. Compound 1 is a liquid at ambient temperature, but 2-4 are crystalline, and solid-state CD-spectroscopy showed that they could be obtained as optically active bulk samples. It should be noted that the optical activity arise upon crystallization, and no optically active precursors were used. Indeed, even commercial samples of 3 and 4 were found to be optically active, giving evidence for the ease at which total spontaneous resolution may occur in certain systems.

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