Editing Swern oxidation (section)

==Considerations==
Dimethyl sulfide, a byproduct of the Swern oxidation, is one of the most notoriously unpleasant odors known in organic chemistry. Humans can detect this compound in concentrations as low as 0.02 to 0.1 parts per million.<ref>{{cite book | author = Morton, T. H. | year = 2000 | chapter = Archiving Odors |editor1=Bhushan, N. |editor2=Rosenfeld, S. | title = Of Molecules and Mind | pages = 205–216 | location = Oxford | publisher = Oxford University Press}}</ref> A simple remedy for this problem is to rinse used glassware with [[bleach]] or [[oxone]] solution, which will oxidize the dimethyl sulfide back to dimethyl sulfoxide or to [[dimethyl sulfone]], both of which are odourless and nontoxic.<ref>{{cite journal |title= Safe Handling of Boranes at Scale | first1=William J. Jr. | last1=Atkins |first2= Elizabeth R. |last2= Burkhardt |first3= Karl |last3= Matos |journal= Org. Process Res. Dev. |year= 2006 | volume= 10 |issue= 6 |pages= 1292–1295 |doi= 10.1021/op068011l}}</ref>

The reaction conditions allow oxidation of acid-sensitive compounds, which might decompose under the acidic oxidation conditions such as [[Jones oxidation]].  For example, in Thompson & Heathcock's synthesis of the [[sesquiterpene]] isovelleral,<ref name="Thompson1992">{{cite journal|last=Thompson|first=S. K.|author2=Heathcock, C. H. |year=1992|title=Total synthesis of some marasmane and lactarane sesquiterpenes|journal=[[J. Org. Chem.]]|volume=57|issue=22|pages=5979–5989|doi=10.1021/jo00048a036}}</ref> the final step uses the Swern protocol, avoiding [[rearrangement reaction|rearrangement]] of the acid-sensitive cyclopropanemethanol moiety.

[[File:IsovelleralPreparationViaSwernOxidation.png|500px|center]]