Abstract
The configurations and preferred conformations in series of 4,5-dialkyl and 4,5,5-trialkylsubstituted 2,2-dimethyl-1,3-dioxanes were studied. It was proved by PMR spectroscopy that the low-boiling isomers have the cis configuration, while the high-boiling isomers have the trans configuration; moreover, all of the isomers are found in the preferred chair conformation. This conformation experiences a certain amount of distortion, the degree of which depends on the number and character of the substituents in the 5 position.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. I. Gren', L. A. Litvinova, S. G. Soboleva, A. V. Bogatskii, and Z. D. Bogatskaya, Material from the 1st All-Union Conference on Dynamic Stereochemistry and Conformational Analysis [in Russian], Odessa (1970), p. 69.
G. I. Goryashina, A. V. Bogatskii, Yu. Yu. Samitov, O. S. Stepanova, and N. I. Karelina, Khim. Geterotsikl. Soedin., 391 (1968).
Z. V. Bogatskii, Yu. Yu. Samitov, S. P. Egorova, and T. A. Zakharchenko, Zh. Organ. Khim., 5, 830 (1969).
Yu. Yu. Samitov, N. L. Garkovik, A. V. Bogatskii, and S. A. Zolotareva, Khim. Geterotsikl. Soedin., 608 (1968).
A. V. Bogatskii, Yu. Yu. Samitov, and Z. D. Bogatskaya, Zh. Organ. Khim., 5, 2230 (1969).
A. V. Bogatskii, Yu. Yu. Samitov, A. I. Gren', and S. G. Soboleva, Khim. Geterotsikl. Soedin., 893 (1971).
A. I. Gren', S. G. Soboleva, and G. F. Tantsyura, in: Problems in Stereochemistry, No. 1 [in Russian], Izd. Kievsk. Univ. (1971).
S. G. Soboleva and A. I. Gren', Zh. Vsesoyuzn. Khim. Obshchestva (in press).
B. Fremaux, M. Davidson, M. Hellin, and E. Coussemant, Bull. Soc. Chim. France, 4243 (1967).
J. P. Maffrand and P. Maroni, Bull. Soc. Chim. France, 1408 (1970).
J. P. Maffrand and P. Maroni, Tet. Letters, 4201 (1969).
K. Maskens, D. E. Minnikin, and N. Polgar, J. Chem. Soc., C, 2113 (1966).
D. Cram and K. Kopesky, J. Am. Chem. Soc., 81, 2748 (1959).
J. H. Stocker, P. Sidisunthorn, B. M. Benjamin, and C. J. Collins, J. Am. Chem. Soc., 82, 3913 (1960).
H. Conroy, in: Advances in Organic Chemistry, Vol. 2, Wiley (1960).
K. Pihlaja and P. Äyräs, Acta Chem. Scand., 24, 531 (1970).
Author information
Authors and Affiliations
Additional information
See [1] for communication XVI.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1464–1468, November, 1972.
Rights and permissions
About this article
Cite this article
Soboleva, S.G., Gren', A.I., Samitov, Y.Y. et al. Stereochemistry of heterocycles. Chem Heterocycl Compd 8, 1321–1325 (1972). https://doi.org/10.1007/BF00471862
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00471862