Journal of Organic Chemistry p. 2777 - 2781 (1986)
Update date:2022-08-11
Topics:
Rafizadeh, Karim
Yates, Keith
A variety of m-nitrobenzyl derivatives including alcohols, alkyl ethers, esters, and an amine undergo photooxidation reactions to produce m-nitrobenzaldehyde (or m-nitroacetophenone in two cases) as the major isolated product.The reaction is both solvent and pH dependent and only takes place in essentially aqueous media.The quantum efficiency of product formation reaches a maximum (φ =0.3-0.4) in the 20-50percent sulfuric acid range, depending on the substrate, although the reaction is reasonably efficient even in neutral aqueous solution.The presence of benzylic hydrogen and a heteroatom (O,N) in the α-position appears to be essential for photooxidation to occur.The multiplicity of the reactive state is T1.A solvent isotope effect (φH2O/φD2O = 1.4) was observed.The proposed mechanism involves rate-determining protonation of T1 followed by rapid α-hydrogen abstraction by water.
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