Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3Z,9Z)‑1,2,5,8-Dithiadiazecine-6,7(5H,8H)‑dione Series

Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3Z,9Z)‑1,2,5,8-Dithiadiazecine-6,7(5H,8H)‑dione Series

For the first time, chirality in (3Z,9Z)-1,2,5,8-dithiadiazecine-6,7­(5H,8H)-dione series was recognized. Enantiomers of the 4,9-dimethyl-5,8-diphenyl analogue were isolated at room temperature, and their thermal stability was determined. X-ray crystallography confirmed the occurrence of a pair of e...

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Veröffentlicht in:Journal of organic chemistry 2018-08, Vol.83 (15), p.7566-7573
Hauptverfasser: Risso, Vesna, Farran, Daniel, Javierre, Guilhem, Naubron, Jean-Valère, Giorgi, Michel, Piras, Patrick, Jean, Marion, Vanthuyne, Nicolas, Fruttero, Roberta, Lorcy, Dominique, Roussel, Christian
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container_end_page 7573
container_issue 15
container_start_page 7566
container_title Journal of organic chemistry
container_volume 83
creator Risso, Vesna
Farran, Daniel
Javierre, Guilhem
Naubron, Jean-Valère
Giorgi, Michel
Piras, Patrick
Jean, Marion
Vanthuyne, Nicolas
Fruttero, Roberta
Lorcy, Dominique
Roussel, Christian
description For the first time, chirality in (3Z,9Z)-1,2,5,8-dithiadiazecine-6,7­(5H,8H)-dione series was recognized. Enantiomers of the 4,9-dimethyl-5,8-diphenyl analogue were isolated at room temperature, and their thermal stability was determined. X-ray crystallography confirmed the occurrence of a pair of enantiomers in the crystal. Absolute configurations were assigned by comparing experimental and calculated vibrational/electronic circular dichroism spectra of isolated enantiomers. A distorted tesseract (four-dimensional hypercube) was used to visualize the calculated enantiomerization process, which requires the rotation around four chirality axes. Conformers of higher energy as well as several concurrent pathways of similar energies were revealed.
doi_str_mv 10.1021/acs.joc.8b01009
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title Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3Z,9Z)‑1,2,5,8-Dithiadiazecine-6,7(5H,8H)‑dione Series
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