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The free radical-mediated deoxygenation of alcohol compounds after the formation of thiocarbonyl intermediates is known as the Barton-MacCombie deoxygenation. This reaction is one of the most popular ways to remove hydroxyl groups.
Alkyl xanthates are used commonly, but phenyl thiocarbonates and thiocarbonyl imidazolates are also reactive substrates.
Trapping the radical intermediate is possible when the reacting molecule contains necessary functional groups. An example of intramolecular radical trapping leading to the formation of a five-membered ring is shown here.
An application found in the total synthesis of azadirachtin.
 Danishefsky, S. J. et al. J. Am. Chem. Soc. 2000, 122, 6160. DOI: 10.1021/ja000521m
 Tadano, K. et al. J. Org. Chem. 1995, 60, 8179. DOI: 10.1021/jo00130a017
 Veitch, G. E.; Beckmann, E.; Burke, B. J.; Boyer, A.; Maslen, S. L.; Ley, S. V. Angew. Chem. Int. Ed. 2007, 46, 7629. DOI:10.1002/anie.200703027