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Updated: Aug 23, 2025

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
[Sulfonyl-bis-(bromo-methyl-ene)]di-benzene
1Department of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA.
The stereochemistry of a dibrominated organic compound was determined using X-ray crystallography. This revealed a 1,3-elimination reaction mechanism involving inversion of configuration at chiral centers.
Area of Science:
- Organic Chemistry
- Crystallography
- Stereochemistry
Background:
- The title compound, C14H12Br2O2S, is a diastereoisomer.
- Understanding the stereochemical outcome of reactions is crucial in organic synthesis.
Purpose of the Study:
- To determine the crystal structure of the title compound.
- To elucidate the mechanism of 1,3-elimination of bromine using triphenylphosphine.
Main Methods:
- Single-crystal X-ray diffraction was employed to determine the molecular structure.
- Analysis of the crystal structure provided insights into the reaction mechanism.
Main Results:
- The compound crystallizes as the meso isomer of a diastereoisomeric pair.
- The 1,3-elimination of bromine by triphenylphosphine proceeds with inversion of configuration at both chiral carbon atoms.
Conclusions:
- The crystal structure determination was essential for understanding the stereochemical course of the elimination reaction.
- Weak intermolecular interactions, including C-H⋯O and C-H⋯Br hydrogen bonds, stabilize the crystal structure.
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