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.
Similar content being viewed by others
References
H. Gilman and F. Breuer, J. Am. Chem. Soc., 55, 1123, 1934.
H. Gilman and R. L. Bebb, J. Am. Chem. Soc., 61, 109, 1939.
A. A. Morton and G. H. Patterson, J. Am. Chem. Soc., 65, 1346, 1943.
V. Ramanathan and R. Levine, J. Org. Chem., 27, 1216, 1962.
W. K. McEven, J. Am. Chem. Soc., 58, 1125, 1936.
Ya. L. Gol'dfarb and Ya. L. Danyushevskii, ZhOKh, 31, 3654, 1961.
A. I. Shatenshtein, Isotopic Exchange and Hydrogen Replacement in Organic Compounds [in Russian], Izd-vo AN SSSR, 1960.
A. I. Shatenshtein, I. O. Shapiro, Yu. I. Ranneva, and A. G. Kamrad, collection: Reactivities of Organic Compounds [in Russian], Izd-vo Tart. GU, 1, 232, 1964.
N. Ya. Turova and A. V. Novoselova, Usp. khim., 34, 385, 1965.
D. J. Cram, C. A. Kingsbury, and A. Langemann, J. Am. Chem. Soc., 81, 5785, 1959.
T. J. Wallace, J. E. Hofmann, and A. Schriesheim, J. Am. Chem. Soc., 85, 2739, 1963.
E. J. Stamhuig, W. Drenth, and H. van der Berg, Rec. trav. chim., 83, 167, 1964.
S. Gronowitz, G. Sörling, B. Gestblom, and R. A. Hoffman, Ark. Kem., 19, 483, 1962.
R. A. Gavar and Ya. P. Stradyn, KhGS, 15, 1965.
H. Gilman and G. F. Wright, J. Am. Chem. Soc., 55, 3302, 1933.
B. Bak, L. Hausen, and J. Rastrup-Anderson, Disc. Farad. Soc., 19, 30, 1955.
L. Berger, A. Zierling, and J. Lee, J. Org. Chem., 12, 904, 1947.
H. Gilman and R. R. Burtner, J. Am. Chem. Soc., 55, 403, 1933.
H. Gilman and R. R. Burtner, J. Am. Chem. Soc., 55, 2903, 1933.
S. M. McElvain and A. H. Bolstad, J. Am. Chem. Soc., 73, 1988, 1951.
I. O. Shapiro, A. G. Kamrad, Yu. I. Ranneva, and A. I. Shatenshtein, Izv. AN LatvSSR, ser. khim., 535, 1964.
Author information
Authors and Affiliations
Additional information
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.
Rights and permissions
About this article
Cite this article
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
Issue Date:
DOI: https://doi.org/10.1007/BF00477500