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- W1999133036 abstract "The Duff reaction of β-naphthol (I) with hexamine in glacial acetic acid at 100° gives 2,2′-dihydroxy-1-naphthylidene-1′-naphthylmethylamine (II), but at lower concentrations of starting materials 2-hydroxy-1-naphthaldehyde (IV) is the main product. The rate law for the latter reaction is expressed as: d[IV]/dt = [I]m[hexamine]n (m ≳ 1, n ∼ ·4). 2-Hydroxy-1-naphthylmethylamine (III) also reacts with hexamine to produce IV, the rate being higher than that of β-naphthol with hexamine. The rate law is a similar type: d[IV]/dt = k′[III]m′ [hexamine]n′ (m′ ≳ 1, n′ ∼ 0·3). The reaction of this amine III with formaldehyde alone also yields IV and this reaction has an induction period. The addition of n-butylamine or ammonia to the system of III-HCl and formaldehyde eliminated the induction period and increased the rate considerably. The addition of tri-n-butylamine to the same system shortened the induction period, but the rate constant was little increased, while addition of β-naphthol had no appreciable effect on the rate. A mechanism involving the fast aminomethylation of β-naphthol and then the rate-determining dehydrogenation of the amine to the imine, followed by the rapid hydrolysis of the imine is proposed and discussed." @default.
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- W1999133036 date "1968-01-01" @default.
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- W1999133036 title "Kinetics and mechanism of the Duff reaction" @default.
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- W1999133036 doi "https://doi.org/10.1016/s0040-4020(01)88408-8" @default.
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