Tetrahedron p. 1091 - 1106 (1988)
Update date:2022-08-04
Topics:
Belavoine, Gilbert
Barton, Derek H. R.
Boivin, Jean
Gref, Aurore
Coupanec, Pascale Le
et al.
Six saturated hydrocarbons (cyclohexane, 3-ethylpentane, methylcyclopentane, cis- and trans-decalin and adamantane) were oxidised by the Gif system (iron catalyst, oxygen, zinc, carboxylic acid) and its electrochemical equivalent (Gif-Orsay system).Results obtained using various solvents (pyridine, acetone, pyridine-acetone mixtures) were similar for both systems.Total or partial replacement of pyridine with acetone affects the selectivity for secondary positions and lowers the ketone/secondary alcohol ratio.The formation of the same ratio of cis- and trans-decal-9-ol from both cis- and trans-decalin clearly demonstrates that tertiary alcohols result from a mechanism essentially radical in nature.
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