A study was made of the isomerization of 1-methyl-1-cyclopentene oxide in the presence of nucleophilic and electrophilic catalysts, and also of its thermal isomerization.
1-Methyl-1-cyclopentene oxide is easily isomerized in the presence of electrophilic catalysts, while in the presence of nucleophilic catalysts it isomerizes only at elevated temperature, with the formation in both cases of a complex mixture of products, in which were identified 2-methylcyclopentanone, its condensation products, representing unsaturated ketones, 2-methylenecyclopentanol, and an unsaturated aldehyde of composition C6H10O.
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L. A. Mukhamedova and M. I. Kudryavtseva, Khim. Geterotsikl. Soedin., 579 (1968).
B. A. Arbuzov, Dissertation [in Russian], Kazan' (1936), p. 209.
G. Chavanne and M. L. de Vogel, Bull. Soc. Chim. Belges,37, 141 (1928).
M. van Rysseiberge, Bull. Schim. Belges,35, 311 (1926).
M. Goryaev and I. Pliva, Methods for Studying Ethereal Oils [in Russian], Izd. AN KazSSR, Alma-Ata (1962), pp. 177, 181.
V. S. Joshi, N. O. Damodaran, and Sukh Dev, Tetrahedron,24, 5817 (1968).
J. K. Crandall and L. H. C. Lin, J. Org. Chem.,33, 2375 (1968).
Houben-Weyl, Methods for Organic Chemistry. Methods of Analysis [Russian translation], Goskhimizdat (1963), p. 460.
E. A. Braude and A. A. Webb, J. Chem. Soc., 3328 (1958).
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 890–896, April, 1972.
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Mukhamedova, L.A., Kudryavtseva, M.I. & Shagidullin, R.R. Isomerization of 1-methyl-1-cyclopentene oxide. Russ Chem Bull 21, 843–848 (1972). https://doi.org/10.1007/BF00854484
- Elevated Temperature