Journal of the Chemical Society. Perkin transactions II p. 1243 - 1246 (1981)
Update date:2022-09-26
Topics:
Butler, Richard N.
Morris, Gerard J.
O'Donohue, Anne M.
The reaction of substituted phenylhydrazones with thallium(III) acetate in acetic acid involved an electrophilic attack at the hydrazone amino-NH moiety giving an intermediate which is attacked by solvent at the methine carbon.The Hammett ρ values for substituents in the methine and the N-phenyl rings were -1.05 and -3.6, respectively.Activation thermodynamic parameters ΔEa 17.9, ΔHa 17.2 kcal mol-1, and ΔSa -14.65 cal K-1 mol-1 were measured for p-chlorobenzaldehyde p-nitrophenylhydrazone.The main products from aromatic aldehyde arylhydrazones were N'-acetyl-N-aroyl-N'-arylhydrazines (5).The main products from ketone arylhydrazones were α-acetoxy-α-phenylazo-derivatives of the ketone (4).The unexpected divergence of reactivity of phenylhydrazones with the acatates of Hg(II), Tl(III), and Pb(IV) is discussed.
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Doi:10.1246/cl.1981.1409
(1981)Doi:10.1248/cpb.29.2442
(1981)Doi:10.1021/jm049651m
(2004)Doi:10.1016/S0040-4039(01)81898-0
(1981)Doi:10.1002/hlca.19810640715
(1981)Doi:10.1016/S0040-4020(01)98922-7
(1981)
