Archive for August 25th, 2023

Pre-mechanism for the Swern Oxidation: formation of chlorodimethylsulfonium chloride.

Friday, August 25th, 2023

The Swern oxidation[cite]10.1016/0040-4020(78)80197-5[/cite] is a class of “activated” dimethyl sulfoxide (DMSO) reaction in which the active species is a chlorodimethylsulfonium chloride salt. The mechanism of this transformation as shown in e.g. Wikipedia is illustrated below. However, an interesting and important aspect of chemistry is not apparent in this schematic mechanism and to rectify this, a full computed mechanism is laid out below, for which the FAIR data has a DOI: 10.14469/hpc/13151
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