Barton–McCombie deoxygenation

E395221

Barton–McCombie deoxygenation is an organic chemistry reaction that converts alcohols into the corresponding hydrocarbons via radical-mediated removal of the hydroxyl group.

All labels observed (1)

Label Occurrences
Barton–McCombie deoxygenation canonical 2

How this entity was disambiguated

Statements (49)

Predicate Object
instanceOf name reaction ⓘ
organic reaction ⓘ
radical reaction ⓘ
appliedIn complex molecule synthesis ⓘ
late-stage functional group manipulation ⓘ
natural product synthesis ⓘ
converts alcohols ⓘ
development photoredox-catalyzed variants ⓘ
tin-free variants ⓘ
field organic chemistry ⓘ
initiationMethod photochemical initiation ⓘ
thermal initiation ⓘ
keyIntermediate carbon-centered radical ⓘ
thiocarbonyl derivative ⓘ
xanthate ester ⓘ
keyStep formation of thiocarbonyl derivative ⓘ
limitation use of toxic organotin reagents ⓘ
mechanism radical-mediated ⓘ
mechanisticStep generation of carbon radical from xanthate ⓘ
homolytic cleavage of C–S bond ⓘ
hydrogen atom abstraction by carbon radical ⓘ
namedAfter Derek H. R. Barton ⓘ
Stuart W. McCombie ⓘ
originalPublicationJournal Journal of the Chemical Society, Perkin Transactions 1 ⓘ
overallEffect replacement of OH by hydrogen ⓘ
product hydrocarbons ⓘ
publicationYear 1975 ⓘ
reactionType deoxygenation ⓘ
relatedReaction Barton decarboxylation ⓘ
radical dehalogenation ⓘ
removes oxygen atom from alcohol ⓘ
selectivity chemoselective for C–O bond reduction ⓘ
stereochemicalOutcome often leads to loss of stereochemistry at carbon center ⓘ
transformsFunctionalGroup hydroxyl group ⓘ
typicalSolvent benzene ⓘ
toluene ⓘ
xylene ⓘ
typicalSubstrate primary alcohol ⓘ
secondary alcohol ⓘ
tertiary alcohol ⓘ
usesHydrogenAtomDonor Bu3SnH ⓘ
organosilane reagent ⓘ
tributyltin hydride ⓘ
tris(trimethylsilyl)silane ⓘ
usesRadicalInitiator AIBN ⓘ
azobisisobutyronitrile ⓘ
usesReagent thiocarbonate reagent ⓘ
thiocarbonylimidazole reagent ⓘ
xanthate reagent ⓘ

How these facts were elicited

Referenced by (2)

Full triples — surface form annotated when it differs from this entity's canonical label.

Derek H. R. Barton → notableWork → Barton–McCombie deoxygenation ⓘ
Barton reaction → relatedReaction → Barton–McCombie deoxygenation ⓘ