Barton Deoxygenation (Barton-McCombie Reaction)

D. H. R. Barton, S. W. McCombie, J. Chem. Soc. Perkin Trans. 1 1975, 1574.

Deoxygenation of alcohols via their thiocarbonyl derivatives which undergo free radical scission upon treatment with tri-n-butyltin hydride:

Mechanistic study: J. E. Forbes, S. Z. Zard, Tetrahedron Lett. 30, 4367 (1989). Review: M. Pereyre et al., Tin in Organic Synthesis (Butterworths, Boston, 1987) pp 84-96. Review of methodological improvements, particularly the replacement of tri-n-butyltin hydride with silicon hydrides: C. Chatgilialoglu, C. Ferreri, Res. Chem. Intermed. 19, 755-775 (1993).