Barton decarboxylation
Reaction
The Barton decarboxylation is a radical reaction in which a carboxylic acid is converted to a thiohydroxamate ester (commonly referred to as a Barton ester). The product is then heated in the presence of a radical initiator and a suitable hydrogen donor to afford the decarboxylated product. This is an example of a reductive decarboxylation. Using this reaction it is possible to remove carboxylic acid moieties from alkyl groups and replace them with other functional groups. (See Scheme 1) This reaction is named after its developer, the British chemist and Nobel laureate Sir Derek Barton (1918–1998).
Mechanism
The reaction is initiated by homolytic cleavage of a radical initiator, in this case 2,2'-azobisisobutyronitrile (AIBN), upon heating. A hydrogen is then abstracted from the hydrogen source (tributylstannane in this case) to leave a tributylstannyl radical that attacks the sulfur atom of the thiohydroxamate ester. The N-O bond of the thiohydroxamate ester undergoes homolysis to form a carboxyl radical which then undergoes decarboxylation and carbon dioxide (CO2) is lost. The remaining alkyl radical (R·) then abstracts a hydrogen atom from remaining tributylstannane to form the reduced alkane (RH). (See Scheme 2) The tributyltin radical enters into another cycle of the reaction until all thiohydroxamate ester is consumed.
This brief starts where responsible research should: with the source description of “Barton decarboxylation” as reaction. Everything that follows is an evidence route, not borrowed authority.
Why this record matters
The subject matters to the general reference register because the source frames it as reaction. Its deeper value depends on whether names, dates, institutions and citations support that framing.
Vocabulary and entity names are the principal evidence signals here, because they determine the precision of every later search. The source revision retrieved here is dated Aug 14, 2026. The linked authority identifier is Q3454335. None of the 0 selected statements returned an explicit reference. The first chronological checks are 1918 and 1998.
A concise general-reference account can conceal disagreements about scope, terminology or the weight assigned to individual sources. The lead is largely declarative, so disagreement and counter-evidence require a deliberate search beyond the opening account. Authority statements aid reconciliation but still require their own references, qualifiers and ranks to be checked.
How to read it
Use the entry as an orientation point, then follow its citations and revision history. Names, dates and institutional relationships should be checked against the original record.
- Subject orientation
- Search vocabulary
- Locating named sources
The closest primary source, responsible institution and strongest cited specialist reference.
Three-step research path
- Establish the record: confirm the title “Barton decarboxylation”, its source revision and the description used here.
- Expand the search: follow Barton decarboxylation primary sources, Barton decarboxylation archive and Barton research across catalogues and specialist indexes.
- Test the account: compare the strongest cited source with the responsible institution’s current record and note any disagreement.
Questions for further research
- Which source most directly establishes the central claim about “Barton decarboxylation”?
- What terminology or title could unlock a more precise catalogue search?
- Which cited source is closest to the event, object or claim?
Search terms from this dossier
This entry incorporates text from “Barton decarboxylation” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.