Spontaneous Generation of Chirality in Simple Diaryl Ethers.
Journal article, 2015

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.

CD-spectroscopy

Author

Anders Lennartsson

Chalmers, Chemistry and Chemical Engineering, Applied Chemistry, Polymer Technology

Anna Hedström

University of Gothenburg

Mikael Håkansson

University of Gothenburg

Chirality

0899-0042 (ISSN) 1520-636X (eISSN)

Vol. 27 7 425-9

Subject Categories

Chemical Sciences

Organic Chemistry

DOI

10.1002/chir.22460

PubMed

26032449

More information

Created

10/8/2017