Barton decarboxylation

[3][4] (See Scheme 1) This reaction is named after its developer, the British chemist and Nobel laureate Sir Derek Barton (1918–1998).

N-O bond cleavage of the Barton ester can also occur spontaneously upon heating or by irradiation with light to initiate the reaction.

In this case a radical initiator is not required but a hydrogen-atom (H-atom) donor is still necessary to form the reduced alkane (RH).

[5] The relative expense, smell, and toxicity associated with tin, thiol or silane reagents can be avoided by carrying the reaction out using chloroform as both solvent and H-atom donor.

[7] The reaction proceeds due to the formation of the stable S-Sn bond and increasing aromaticity of the thiohydroxamate ester.