Conclusions
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1.
The conformations of 2-benzylidenecyclohexanone, its 2-p-halo-derivatives, and pulegone were investigated by the method of dipole moments (DM). These compounds have a half-chair conformation, while the phenyl radical in the benzylidene derivatives occupies a trans-position relative to the carbonyl group.
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2.
For 2,6-dibenzylidenecyclohexanone and its 2,6-di-p-halo-derivatives, an envelope-type conformation was demonstrated, according to the data of DM and IR spectroscopy.
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3.
For benzylidenecyclohexanone oxide, a chair conformation with an axial oxygen atom of the epoxy group is preferential.
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Literature cited
N. L. Allinger, J. Amer. Chem. Soc.,81, 5727 (1959).
J. Dale, J. Chem. Soc., 1028 (1965).
A. C. Huitric and W. D. Kumler, J. Amer. Chem. Soc.,78, 614, 1147 (1956).
J. F. Böeseken, Recueil. Trav. Chim.,56, 1203 (1937).
W. Doben and J. Pitzer, Steric Effects in Organic Chemistry [Russian translation] (Newman, editor), IL (1960).
B. Ottar, Acta Chem. Scan.,1, 283 (1947).
C. W. Beckett, N. K. Freeman, and K. S. Pitzer, J. Amer. Chem. Soc.,70, 4227 (1948).
J. B. Bentley, K. B. Everard, K. J. B. Marsden, and E. L. Sutton, J. Chem. Soc., 2957 (1949).
H. O. House and R. L. Wallson, J. Amer. Chem. Soc.,78, 4394 (1956).
M. Horak and P. Munk, Collect. Czechoslov. Chem. Commun.,24, 3024 (1959).
J. M. Hendricson, J. Amer. Chem. Soc.,83, 4537 (1961).
V. Baliash and K. Aparajithan, Tetrahedron,19, 2177 (1963).
A. A. Gribov and E. M. Popov, Dokl. Akad. Nauk SSSR,145, 761 (1962).
P. W. Allen and L. E. Sutton, Acta Crystallogr.,3, 46 (1950).
S. O'Connor, W. J. O'Sillivan, E. M. Phibbin, and C. P. Lillya, Chem. and Industr., 1925 (1966).
R. Bramley and R. J. W. LeFevre, J. Chem. Soc., 56 (1962).
G. V. Pugilevskii and I. K. Mironova, Zh. Obshch. Khim.,27, 1101 (1957).
W. Reusch and C. K. Johnson, J. Organ. Chem.,28, 2557 (1963).
J. C. Sheehen and R. M. Wilson, J. Amer. Chem. Soc.,89, 3457 (1967).
K. J. Carlson and N. S. Behn, J. Organ. Chem.,32, 1363 (1967).
H. F. Zimmerman, L. Linger, and B. S. Thygarajan, J. Amer. Chem. Soc.,81, 108 (1959).
F. D. Ganston, Uspekhi Organ. Khimii,1, 146 (1963).
W. S. Emmerson and G. H. Birum, J. Amer. Chem. Soc.,75, 1312 (1953).
B. A. Arbuzov and L. K. Yuldasheva, Izv. AN SSSR. Otd. Khim. N., 1728 (1962).
E. J. Corey and R. A. Sneen, J. Amer. Chem. Soc.,77, 2505 (1955).
F. Brutcher and W. Bauer, J. Amer. Chem. Soc.,84, 2233 (1962).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1011–1016, May, 1969.
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Arbuzov, B.A., Yuldasheva, L.K. & Arshinova, R.P. Conformation of benzylidenecyclohexanone, dibenzylidenecyclohexanone, and benzylidenecyclohexanone oxide. Russ Chem Bull 18, 923–927 (1969). https://doi.org/10.1007/BF00922842
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DOI: https://doi.org/10.1007/BF00922842