The BartonMcCombie protocol for the deoxygenation of alcohols 4, 5 is an extremely useful method that has found widespread application in synthetic organic chemistry. 6 This radicalmediated process typically employs 1. 53 equiv of Bu 3 SnH 7 as the reducing agent. A Guide to Using Reaxys 2 CONTENTS Accessing Reaxys 3 Performing a Search 6 Reaction search based on the reaction BartonMcCombie deoxygenation Citation search in the title, abstract and keyword based on the term arton Mc ombie FULL TEXT in this manual).
Performing a Search A classical radical deoxygenation reaction using overstoichiometric amounts of highly noxious chemicals is the BartonMcCombie reaction, although nowadays several improved protocols are A.
A TwoStep Sequence. In 1975 Barton and McCombie reported a twostep sequence for hydroxylgroup replacement by a hydrogen atom. 1 The first step in this process was the conversion of the hydroxyl group into an Othiocarbonyl group, and the second step (the BartonMcCombie reaction) was a freeradical chain reaction that replaced the Othiocarbonyl group with a hydrogen atom. The BartonMcCombie deoxygenation is an organic reaction in which a hydroxy functional group in an organic compound is replaced by a hydrogen to give an alkyl group.
[1 [2 It is named after British chemists Sir Derek Harold Richard Barton ( ) and Stuart W. McCombie. Since its introduction by Barton and McCombie, the deoxygenation of thionocarbonyl derivatives of alcohols has become an important synthetic reaction and a valuable method for the generation of carboncentered radicals.
3, 4 5 Xanthates, thionobenzotes, thionocarbonyl imidazolides, aryloxy thionocarbonate, and oxalate The BartonMcCombie reaction is the deoxygenation of an aliphatic alcohol via thioacylation of the alcohol followed by radical cleavage.
Variations of the reaction may employ different thioacyl fragments and hydrogen sources, although Smethyl xanthates and tributylstannane are most commonly used. BartonMcCombie Reaction Barton Deoxygenation. A method for the deoxygenation of alcohols. The alcohol is first converted to the thiocarbonyl derivative, and is then treated with Bu 3 SnH. Once the radical chain has been initiated, attack on the Bu 3 Sn carrier by sulphur initiates a decomposition yielding the alkyl radical, for which Bu 3 SnH serves as hydrogen radical (H) donor.