R. Yoshizawa, T. Inukai
Nov 1, 1969
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Journal
Bulletin of the Chemical Society of Japan
Abstract
Peroxy-trans-crotonic acid was prepared from dicrotonyl peroxide by alkaline cleavage and isolated for the first time in a crystalline state, mp 41–42°C. It was characterized by NMR and IR spectra, and its stability briefly tested. Reaction with dimethyl sulfide gave a quantitative yield of crotonic acid. Its pKa in water at 25°C was 8.2. Second order rate constants of reaction with crotonaldehyde in benzene (Table 4) were measured: Ea, 13.3 kcal/mol; log A(l/mol sec), 5.3; ΔS\eweq, −36 eu/mol. Detection of a possible intermediate, a peracid-aldehyde complex X, was attempted by means of NMR but evidence for it was not obtained.