Related Experiment Video

Updated: Jun 5, 2025

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
07:12

Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions

Published on: July 17, 2020

6.2K

3aH,4H,5H,8H,9H,9aH-Cyclo-octa-[d][1,3]dioxole-2-thione

Dieter Schollmeyer1, Claudia Kammler1, Heiner Detert1

  • 1University of Mainz, Department of Chemistry, Duesbergweg 10-14, 55099 Mainz, Germany.

Iucrdata
|December 9, 2024
PubMed

Insights

The thio-nocarbonate of trans-cyclo-octenediol crystallizes with significant enantiomeric disorder. This structural characteristic, arising from trans-annulation, forces both rings into a twist conformation.

Area of Science:

  • Organic Chemistry
  • Crystallography
  • Stereochemistry

Background:

  • The study investigates the solid-state structure of a specific thio-nocarbonate compound.
  • Understanding molecular conformation and enantiomeric interactions is crucial in organic chemistry.

Purpose of the Study:

  • To determine the crystal structure of the thio-nocarbonate of trans-cyclo-octenediol.
  • To analyze the conformational preferences and stereochemistry of the molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the crystalline structure.
  • The crystallographic data was used to model the molecular geometry and disorder.

Main Results:

  • The compound, C9H12O2S, exhibits a 9/1 disorder between the R,R and S,S enantiomers.
  • The trans-annulation within the molecule leads to both rings adopting a twist conformation.

Conclusions:

  • The crystallization behavior reveals significant enantiomeric disorder in the solid state.
  • The inherent strain from trans-annulation dictates a non-planar, twist conformation for the cyclo-octene rings.

Keywords:
crystal structureheterocyclessulfur

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