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Kinetics of deuterium exchange of furan and methylfurans in dimethylsulfoxide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Rates of exchange between deuterium in 2D-, 3D-, 2D-3CH3-, and 2D-5CH3 -furan and a solution of potassium tert-butoxide in dimethylsulfoxide are measured. Protophilic deuterium exchange at position 2 in the furan molecule is 600 times faster than that at position 3, while a methyl group at position 3 or 5 retards it 10-fold. Catalytic activities of potassium and lithium butoxides are compared.

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We thank A. E. Berzin for supplying 3-chloromercurifuran, and P. P. Alikhanov and L. Ya. Mashkova for checking the purities of the compounds by GLC.

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Shatenshtein, A.I., Kamrad, A.G., Shapiro, I.O. et al. Kinetics of deuterium exchange of furan and methylfurans in dimethylsulfoxide. Chem Heterocycl Compd 2, 489–492 (1966). https://doi.org/10.1007/BF00477500

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