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Reactions of 1-chloro-2,3-epoxy-2-methylpropane with lower aliphatic alcohols. II. Kinetics

J. Svoboda and V. Macho

Research Institute for Petrochemistry, 972 71 Nov√°ky


Abstract: The reaction of 1-chloro-2,3-epoxy-2-methylpropane with aliph. alcs. in the presence of F3B.Et2O catalyst is first order with respect to the epoxide. The reaction rate is proportional to the effective catalyst concn. and increases with an initial molar ratio of MeOH to epoxide until the value of about 10 is achieved; then it is almost const. From the temp. dependence of the rate consts. the parameters of Arrhenius equation were calcd. The ratio of the products, 1-alkoxy-3-chloro-2-methyl-2-propanols and 2-alkoxy-3-chloro-2-methyl-1-propanols, decreases with increasing temp. and increases with the length and the degree of branching of the hydrocarbon chain of the alc. The activation entropies confirm the SN2 mechanism of the reaction.

Full paper in Portable Document Format: 332a259.pdf


Chemical Papers 33 (2) 259–269 (1979)

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