Tetrahedron p. 2853 - 2872 (1987)
Update date:2022-07-29
Topics: Hydrogen peroxide Precursors Catalysed α,β-unsaturated aldehydes Benzene seleninic acids
Syper, Ludwik
Oxidation of α,β-unsaturated aldehydes with hydrogen perixide catalysed by benzeneselenic acids and their precursors has been investigated.Bis 2-nitrophenyl diselenide has proved to be the most effective catalyst.The major products resulting from the oxidation are vinyl formates (a) which on hydrolysis give saturated aldehydes or ketones (g) having the carbon chain shortened by one carbon atom, compared with the starting aldehydes.The minor products are formyloxyoxiranes (b), α-hydroxycarbonyl (e) and α-formyloxycarbonyl (f) compounds with the carbon chain shortened by one carbon atom.Carbonyl compounds d, formally derived from an oxidative fission of the carbon-carbon double bond, have been also isolated.Diformyloxy (4c) and formyloxyacetoxy phenylmethane (5c) have been isolated when cinnamaldehyde (4) or 1-phenyl-2-formyloxypropane (5a) were oxidized, respectively.Possible mechanisms of formation of these products are discussed.Similar products resulted when α,β-unsaturated aldehydes were oxidized with organic peroxy acids.
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