Summary
A study was made of the isomerization of 2,3-epoxypinane and 3,4-epoxycarane by means of lithium diethylamide. 2,3-Epoxypinane is isomerized into trans-2(10)-pinen-3-ol, whereas 3,4-epoxycarane forms a mixture of alcohols: 3(10)-caren-4-ol, p-mentha-1,5-dien-8-ol, and m-mentha-4,6-dien-2-ol.
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Literature cited
Jörlander, Ber.,50, 406 (1917).
A. C. Cope and B. D. Tiffany, J. Amer. Chem. Soc.,73, 4158 (1951).
A. C. Cope, P. A. Trumbull, and E. R. Trumbull, J. Amer. Chem. Soc.,80, 2844 (1958).
L. J. Haynes, J. Heilbron, E. R. H. Jones, and F. Sondheimer, J. Chem. Soc.,1947, 1583.
A. C. Cope, H. H. Lee, and H. E. Petree, J. Amer. Chem. Soc.,80, 2849 (1958).
A. C. Cope, M. Brown, and H. H. Lee, J. Amer. Chem. Soc.,80, 2855 (1958).
S. Winstein and R. Henderson, Heterocyclic Compounds [Russian translation], IL, Moscow, Vol. 1 (1952), p. 40.
N. A. Prilezhaev, Ber.,42, 4814 (1909).
G. A. Rudakov and M. M. Shestaeva, Zh. obshch. khimii,26, 2357 (1956).
B. A. Arbuzov, Z. G. Isaeva, and V. V. Ratner, Dokl. AN SSSR,134, 583 (1960).
B. A. Arbuzov, Z. G. Isaeva, and V. V. Ratner, Izv. AN SSSR. Otd. khim. n.,1962, 644.
Z. G. Isaeva, B. A. Arbuzov, V. V. Ratner, and I. P. Povodyreva, Izv. AN SSSR. Ser. khim.,1965, 466.
Z. G. Isaeva, B. A. Arbuzov, and V. V. Ratner, Izv. AN SSSR Ser. khim.,1965, 475.
B. A. Arbuzov, Z. G. Isaeva, and N. D. Ibragimova, Izv. AN SSSR, Otd. khim. n.,1962, 649.
B. A. Arbuzov, Z. G. Isaeva, and M. G. Gubaidullin, Izv. AN SSSR, Set. khim.,1965, 678.
M. Yu. Lukina, Uspekhi khimii,31, 901 (1962).
I. N. Nazarov and L. B. Fisher, Izv. AN SSSR. Otd. khim. n.,1945, 631;1948, 436.
H. Gilman and R. G. Tönes, Organ Reactions,6, 339 (1951).
H. Schmidt, Ber.,77, 167 (1944); J. Simonsen, The Terpenes, Cambridge,2 (1957), p. 222.
R. N. Moore, C. Golumbic, and G. S. Fisher, J. Amer. Chem. Soc.,78, 1173 (1956).
B. A. Arbuzov and Z. G. Isaeva, Dokl. AN SSSR,122, 73 (1958).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 838–843, May, 1965 Original article submitted April 22, 1963
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Arbuzov, B.A., Isaeva, Z.G. & Andreeva, I.S. Isomerization of 2,3-epoxypinane and 3,4-epoxycarane by lithium diethylamide. Russ Chem Bull 14, 813–816 (1965). https://doi.org/10.1007/BF00845693
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DOI: https://doi.org/10.1007/BF00845693