Home || Mechanism || NMR || Experimental || References || Leading Questions || About Us || SSG Home

Please note: our section of the article did not have any direct citations within the text. These are all articles that utilize a similar procedure.

Article 1: Concerning the Barton-McCombie Deoxygenation (Step 2)

Barton, D. H. R.; McCombie, S. W. J. Chem. Soc.1975, 16, 1574– 1585.

Article 2: Concerning the Barton-McCombie Deoxygenation (Step 2)

Zhao, G.; Lou, Y.; Zhang, L.; Shao, H.; Xu, W. Synthetic Communications 2012, 42, 2885-2893.

Article 3: Concerning the Synthesis of Tetracyclic Core

Nicolaou, K.C., Scott, G. T, David, J. E. Angew. Chem. Intl. Ed. 2008, 47, 1780-1783.  

Concerning the Barton-McCombie Deoxygenation (Article 1, Step 2)
The Barton-McCombie deoxygenation reaction replaces a hydroxy group with a hydrogen to give an alkyl group. The problem being addressed in this research is the deoxygenation of secondary hydroxy-groups attached to carbon atoms where the SN2 processes are hindered. Many secondary hydroxy-groups in sugar chemistry are considered to be in this category, so this reaction is of importance. In chemistry, there is a need for a reaction where a secondary alcohol is replaced by a hydrogen without rearrangement being possible. On reaction with tributylstannane, U-cycloalkyl thiobenzoates and O-cycloalkyl S-methyl dithiocarbonates, derived from secondary alcohols, gave good yields of the corresponding hydrocarbons. The mechanism of this reaction is radical in character and thus rearrangements common in carbocation reactions are avoided. The reaction takes place under neutral conditions compatible with the presence of the functional groups which normally occur in aminoglycoside antibiotics. A convenient general synthesis of O-cycloalkyl thioesters was developed in this reaction that gave access to U-cycloalkyl thioformates and thioacetates. An extension of this method affords the unknown O-cycloalkyl selenoformates and selenobenzoates. An attempted extension of the method to the synthesis of O-cholesteryl tellurobenzoate gave a good yield of benzyl cholesteryl ether.

Citing the Barton-McCombie article above (Uses of Article 1 Above):


The authors chose to cite this article because in the synthesis of glycoconjugate benzothiazoles, one of the intermediate steps involves the possibility of the formation of a deoxy product. The authors basically used this article in order to disprove the possibility of the formation of the undesired product.


The authors chose to cite this article because in their synthesis of 4,8,12-trimethylnonadecanols, they desired a ‘reliable synthesis of saturated oligoisoprenoids.’ This method, developed by Barton and McCombie, provides such a mechanism to allow the removal of ‘tags’ on the molecule in an efficient and effective manner.


The authors chose to cite this article because in their synthesis of icednine, the authors needed an efficient method in deoxygenating the azido-thiocarbonate and the Barton-McCombie method is a perfect reaction to do so. Mixing the azido-thiocarbonate with excess tributyltin hydride and  AIBN in toluene reduced the thiocarbonate and azide functional groups, which is just a simple modification of Barton and McCombie’s original procedure.