What is it about?
A deformity in the electrostatic potential of chlorine, known as sigma-hole, allows chlorine to act as a positive charge and not as a negative one. We took advantage of this feature to remove chlorine atoms with negatively charged sulfur atoms. We have thus unlocked a chemical reactivity feature in CCl3 groups that can be versatilly used.
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Why is it important?
We can now use a new approach to reactivity of atoms in molecules which were thought to be negative as positive, this way we can now expand the toolbox of reactions for creating more complex molecules.
Read the Original
This page is a summary of: Reactivity of electrophilic chlorine atoms due to σ-holes: a mechanistic assessment of the chemical reduction of a trichloromethyl group by sulfur nucleophiles, Physical Chemistry Chemical Physics, January 2016, Royal Society of Chemistry, DOI: 10.1039/c6cp04321f.
You can read the full text:
New paper in PCCP: CCl3 reduced to CH3 through σ-holes
I found it surprising that the trichloromethyl group could be chemically reduced into a methyl group quite rapidly in the presence of thiophenol, but once again a failed reaction in the lab gave us the opportunity to learn some nuances about the chemical reactivity of organic compounds. Even more surprising was the fact that this reduction occurs through a mechanism in which chlorine atoms behave as electrophiles and not as nucleophiles.
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