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