Atropisomerism in a 10-Membered Ring with Multiple Chirality Axes: (3Z,9Z)-1,2,518-Dithiadiazecine-6,7(5H,8H)-dione Series

被引：3

作者：

Risso, Vesna ^{[1
]}

Farran, Daniel ^{[1
]}

Javierre, Guilhem ^{[1
]}

Naubron, Jean-Valere ^{[2
]}

Giorgi, Michel ^{[2
]}

Piras, Patrick ^{[1
]}

Jean, Marion ^{[1
]}

Vanthuyne, Nicolas ^{[1
]}

Fruttero, Roberta ^{[3
]}

Lorcy, Dominique ^{[4
]}

Roussel, Christian ^{[1
]}

机构：

[1] Aix Marseille Univ, iSm2, Cent Marseille, CNRS, Marseille, France

[2] Aix Marseille Univ, Spectropole, CNRS FR 1739, F-13397 Marseille 20, France

[3] Univ Torino, Dept Drug Sci & Technol, I-810124 Turin, Italy

[4] Univ Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 15期

关键词：

CHIROPTICAL PROPERTIES; ABSOLUTE-CONFIGURATION; DERIVATIVES; OXYGEN; DONOR; DITHIADIAZAFULVALENE; SEPARATION; OXIDATION; ROTATION; COMPLEX;

D O I：

10.1021/acs.joc.8b01009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

For the first time, chirality in (3Z,9Z)-1,2,5,8-dithiadiazecine-6,7(SH,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.

引用

页码：7566 / 7573

页数：8

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