The Barton decarboxylation is a radical reaction in which a carboxylic acid is converted to a thiohydroxamate ester (commonly referred to as a Barton ester). The product is then heated in the presence of a radical initiator and a suitable hydrogen donor to afford the decarboxylated product.[1][2] This is an example of a reductive decarboxylation. Using this reaction it is possible to remove carboxylic acid moieties from alkyl groups and replace them with other functional groups.[3][4] (See Scheme 1) This reaction is named after its developer, the British chemist and Nobel laureate Sir Derek Barton (1918–1998).
Scheme 1
^Barton, D. H. R.; Crich, D.; Motherwell, W. B. (1983). "New and improved methods for the radical decarboxylation of acids". J. Chem. Soc., Chem. Commun. (17): 939. doi:10.1039/C39830000939.
^Barton, D. H. R.; Crich, D.; Motherwell, W. B. (1983). "A practical alternative to the hunsdiecker reaction". Tetrahedron Letters. 24 (45): 4979. doi:10.1016/S0040-4039(01)99826-0.
^Barton, D. H. R.; Crich, D.; Motherwell, W. B. (1985). "The invention of new radical chain reactions. Part VIII. Radical chemistry of thiohydroxamic esters; A new method for the generation of carbon radicals from carboxylic acids". Tetrahedron Letters. 41 (19): 3901. doi:10.1016/S0040-4020(01)97173-X.
^Barton, D. H. R.; Bridon, D.; Zard, S. Z.; Fernandaz-Picot, I. (1987). "The invention of radical reactions Part XV.1 Some mechanistic aspects of the decarboxylative rearrangement of thiohydroxamic esters". Tetrahedron. 43 (12): 2733. doi:10.1016/S0040-4020(01)86878-2.
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