Kinetics and mechanism of acid hydrolysis of peroxyketals |
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| Authors: | V L Antonovskii E V Fedorova I S Kislina N E Shtivel' Yu D Emelin |
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| Institution: | (1) N. N. Semenov Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow;(2) Novokuibyshevsk Branch, All-Union Scientific-Research Institute of Organic Synthesis, USSR |
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| Abstract: | The kinetics of hydrolysis of aliphatic ketone di-tert-butylperoxyketals R1R2C=O, R1, R2=CH3, CH3; CH3, C2H5; CH3, n-C3H7; CH3, n-C6H13; CH3, i-C5H10; CH3, i-C4H9; C2H5, i-C3H7; n-C4H9, n-C4H9; CH3, C6H5-CH2, in dioxane in the presence of H2SO4 were investigated by IR spectroscopy. It was found that the reaction is reversible and takes place according to the equation R1R2C· (OOC(CH3)3)2 + H2O;H+ R1R2C=O + 2HOOC(CH3)3. The proposed mechanism of hydrolysis includes the fast, quasiequilibrium formation of protonated peroxyketal and subsequent formation of the alkylperoxycarbenium ion. A three-parameter correlation equation is proposed for describing the initial rates of hydrolysis of R1R2C(oo-t-Bu)2 peroxyketals.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2501–2506, November, 1990. |
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