Barton Reaction

D. H. R. Barton et al., J. Am. Chem. Soc. 82, 2640 (1960); 83, 4076 (1961).

Conversion of a nitrite ester to a γ-oximino alcohol by photolysis involving the homolytic cleavage of a nitrogen-oxygen bond followed by hydrogen abstraction:



M. Akhtar, Advan. Photochem. 2, 263 (1964); R. H. Hesse, Advan. Free Radical Chem. 3, 83 (1969); J. Kalvoda, Angew. Chem. Int. Ed. 8, 525 (1964). Mechanism: D. H. R. Barton et al., J. Chem. Soc. Perkin Trans. I 1979, 1159. Synthetic application: A. Herzog et al., Angew. Chem. Int. Ed. 37, 1552 (1998).