Abstract
Benzofurans are arranged in the order 2-methylbenzofuran > 3-methylbenzofuran > benzofuran with respect to the case with which they undergo ionic hydrogenation. Benzofuran and 2-methylbenzofuran are protonated in the 3 position of the heterocyclic ring, whereas 3-methylbenzofuran is protonated in the 2 position. Individual monodeuterated 2,3-dihydrobenzofurans can be obtained in high yields by ionic hydrogenation.
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Z. N. Parnes, V. A. Budylin, E. Yu. Beilinson, and A. N. Kost, Zh. Organ. Khim., 8, 2564 (1972).
Z. N. Parnes, G. I. Bolesova, A. I. Belen'kii, and D. N. Kursanov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1918 (1973).
É. A. Karakhanov, E. A. Dem'yanova, L. N. Borodina, and E. A. Viktorova, Dokl. Akad. Nauk SSSR, 214, 584 (1974).
L. Klasing, E. Pop, and N. Trinaistic, Tetrahedron, 28, 3465 (1972).
R. D. Brown and B. A. Coller, Austral. J. Chem., 12, 152 (1959).
R. Royer and J. Rem, Bull. Soc. Chim., France, 1029 (1970).
M. W. Farror and R. Levine, J. Amer. Chem. Soc., 72, 4433 (1950).
Q. M. Brooke, B. S. Furmis, and W. K. R. Musgrave, J. Chem. Soc., 580 (1968).
É. A. Karakhanov, S. V. Lysenko, V. V. Berentsveig, P. A. Sharbatyan, E. A. Viktorova, and A. P. Rudenko, Zh. Khim., 48, 2072 (1974).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1479–1481, November, 1975.
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Karakhanov, É.A., Dem'yanova, E.A., Shkarin, E.G. et al. Ionic hydrogenation of benzofurans. Chem Heterocycl Compd 11, 1261–1263 (1975). https://doi.org/10.1007/BF00474449
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DOI: https://doi.org/10.1007/BF00474449