Tetrahedron p. 14673 - 14688 (1996)
Update date:2022-07-29
Topics:
Barton, Derek H. R.
Jaszberenyi, Joseph Cs.
Liu, Wansheng
Shinada, Tetsuro
Various hydrazone derivatives of α-keto esters were prepared. The carbonyl group was readily regenerated in high yield from phenylhydrazones through oxidative hydrolysis using hypervalent organoiodine(III) reagents either bis(trifluoroacetoxy)-iodobenzene (BTIB) in aqueous acetonitrile or hydroxy(tosyloxy)iodobenzene (HTIB) in chloroform. α-Acotxy phenyl- or methylazo compounds were readily synthesized by oxidation of the corresponding hydrazones with iodobenzene diacetate (IBDA) in dichloromethane or acetic acid. α-Methoxy phenyl- or methylazo compounds were also prepared by oxidation of the hydrazones in methanol. The mechanisms of the oxidation reactions are discussed.
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