Conclusions
-
1.
The NMR spectra of four configurational isomers of 2,6-dimethyl-1-nitro-3-cyclohexenes were studied. The chemical shifts of the signals from all the protons were found, the rate constants of interaction of the vicinal, allyl, and homoallyl protons were determined.
-
2.
The conformation of the molecules of these isomers was established. The relative fraction of conformers in the trans-cis isomer was estimated.
-
3.
The coefficients in the stereochemical dependence for the vicinal (H-Csp2-Csp3-H) and allyl interaction constants were refined.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
G. A. Bottomley and P. R. Jefferies, Austral. J. Chem.,14, 657 (1961).
W. Klyne and V. Prelog, Experientia,16, 521 (1960).
A. I. Kitaygorodsky, Tetrahedron,9, 183 (1960).
F. A. L. Anet and M. Z. Hag, J. Amer. Chem. Soc.,87, 3147 (1965).
C. W. Beckett, N.K. Freeman, and K. S. Pitzer, J. Amer. Chem. Soc.,70, 4227 (1948).
R. Bucourt and D. Hainaut, Bull. Soc. Chim. France, 1366 (1965).
R.J. Abraham, H. Gottschalk, H. Paulsen, and W. A. Thomas, J. Chem. Soc., 6268 (1965).
N. S. Zefirov, V. N. Chekulaeva, and A. I. Belozerov, Zh. Organ. Khim.,5, 630 (1969).
N. S. Zefirov, V. N. Chekulaeva, and A. I. Belozerov, Tetrahedron,25, 1997 (1969).
E. W. Garbish, J. Amer. Chem. Soc.,86, 5561 (1964).
M. Barfield, J. Chem. Phys.,41, 3825 (1964).
A. A. Bothner-By, Advances in Magnetic Resonance, Acad. Press, New York (1965), p. 228.
G. P. Kugatova-Shemyakina, G. M. Nikolaev, and V. M. Andreev, Tetrahedron,23, 2721 (1967).
N. Bhakka and D. Williams, The Use of NMR in Organic Chemistry [Russian translation], Mir (1966), p. 3.
M. L. Huggins, J. Amer. Chem. Soc.,75, 4123 (1953).
G. P. Newsoroff and S. Sternhell, Tetrahedron Letters, 611 (1968).
A. C. Huitric, J. B. Carr, W. F. Trager, and B. J. Nist, Tetrahedron,19, 2145 (1963).
K. S. Ramey and J. Messick, Tetrahedron Letters, 4423 (1965).
Author information
Authors and Affiliations
Additional information
Deceased.
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2473–2481, November, 1971.
Rights and permissions
About this article
Cite this article
Sheichenko, V.I., Nikolaev, G.M., Dubrovina, N.I. et al. NMR spectra and conformation of 2,6-dimethylnitro-3-cyclohexenes. Russ Chem Bull 20, 2347–2353 (1971). https://doi.org/10.1007/BF00854311
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00854311