Conclusions
-
1.
The structure of 5-substituted 2,2-dimethyl-1,3,2-dioxasilanes was studied by the methods of dipole moments and PMR spectroscopy. The compounds have a predominant chair conformation.
-
2.
In the case of 2,2-dimethyl- and 2,2,5-trimethyl-5-nitro-1,3,2-dioxasilane, a conformational equilibrium can exist, strongly shifted in the direction of the conformation with an axial nitro group.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
N. G. Bokii and Yu. T. Struchkov, Zh. Strukt. Khim.,9, 722 (1968).
R. O. Sauer and D. J. Mead, J. Am. Chem. Soc.,68, 1794 (1946).
J. D. Roberts, E. A. McElhill, and R. Armstrong, ibid.,71, 2923 (1949); H. O. Spauschus, A. P. Mills, J. M. Scott, and C. A. McKenzie, ibid.,72, 1377 (1950).
H. Freiser, R. Charles, J. Speier, and M. Eagle, ibid.,73, 5229 (1951); H. Freiser, M. V. Eagle, and J. Speier, ibid.,75, 2821 (1953); A. M. Coleman and H. Freiser, ibid.,83, 4127 (1961).
A. P. Altshuller and L. Rosenblum, ibid.,77, 272 (1955).
R. S. Holland and C. P. Smyth, ibid.,77, 268 (1955); A. J. Petro and C. P. Smith, ibid.,79, 6147 (1957).
J. Karita and M. Kondo, Bull. Chem. Soc., Japan,27, 160 (1964); K. Matsumura, ibid.,35, 801 (1962).
T. Urbanski, D. Gürne, R. Kolinski, H. Piotrowska, A. Jonezyk, B. Serafin, M. Szretter-Szmid, and M. Witanowska, Nitro Compounds, Proc. Intern. Symp. Warszaw (1963), p. 195.
B. A. Arbuzov, I. E. Kovalev, E. N. Tikhomirova, M. G. Voronkov, and L. Zagat, Dokl. Akad. Nauk SSSR,174, 320 (1967).
D. C. McKean, J. Am. Chem. Soc.,77, 2660 (1955).
O. A. Osipov and V. I. Minkin, Handbook of Dipole Moments [in Russian], Vysshaya Shkola (1965).
C. A. Coulson and M. T. Rogers, J. Chem. Phys.,35, 593 (1961).
A. A. Gribov and E. M. Popov, Dokl. Akad. Nauk SSSR,145, 761 (1962).
K. A. Andrianov, B. D. Lavrukhin, É. I. Fedin, and A. A. Zhdanov, ibid.,173, 331 (1967).
F. R. Jensen and C. H. Bushweller, Tetrahedron Letters, 2825 (1968).
A. F. Skryshevskii, V. P. Klochkov, and Yu. V. Pasechnik, Zh. Strukt. Khim.,2, 140 (1961).
K. Jamasaki, A. Kotera, M. Jokoi, and J. Ueda, J. Chem. Phys.,18, 1414 (1950); A. N. Lazarev, Izv. Akad. Nauk SSSR, Ser. Khim., 235 (1964).
E. Eliel, N. Allinger, S. Angyal, and G. Morrison, Conformational Analysis [Russian translation], Mir (1969).
M. Aroney and R. J. W. Le Fevre, J. Chem. Soc., 3600 (1960).
M. G. Voronkov, V. A. Pestunovich, and Yu. P. Romadan, Khim. Geterotsikl. Soed., 178 (1969).
J. E. Andersen, J. Chem. Soc., B, 712 (1967).
Yu. Yu. Samitov, Z. I. Zelikman, and V. G. Kul'nevich, Zh. Strukt. Khim.,10, 234 (1969).
M. G. Voronkov and Yu. P. Romadan, Khim. Geterotsikl. Soed., 879 (1966).
B. A. Arbuzov and L. K. Yuldasheva, Izv. Akad. Nauk SSSR, Otd. Khim., 1728 (1962).
E. A. Corey and R. A. Sneen, J. Am. Chem. Soc.,77, 2505 (1955).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 323–329, February, 1974.
Rights and permissions
About this article
Cite this article
Yuldasheva, L.K., Arshinova, R.P., Samitov, Y.Y. et al. Steric structure of 5-substituted 2,2-dimethyl-1,3,2-dioxasilanes. Russ Chem Bull 23, 294–299 (1974). https://doi.org/10.1007/BF00924672
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00924672