Barton Decarboxylation

The radical decarboxylation of a Barton ester proceeds to the corresponding alkane after treatment with tributyltin hydride or t-butylmercaptan

An alternative possibility is the introduction of a substituent by reaction with a suitable radical trapping agent:

Mechanism of the Barton Decarboxylation

The initiation of the Barton Decarboxylation ( Bu₃Sn-H -> Bu₃Sn^. ) is effected with a radical initiator, and as with the Barton-McCombie Deoxygenation, the driving force for the reaction itself is the formation of the stable S-Sn bond.