Conclusions
-
1.
The automatic assembly of dilactones from α,α′-dihydroxyglutaric acids and their derivatives is controlled not only by configuration (from the d, ℓ and not the meso form) but also by conformation and is not realized in the presence of α,α′-substituents having predominantly pseudoequatorial orientation in the corresponding monolactone. Thus, γ-crotonolactone is formed instead of the expected dilactone during the thermolysis of d,ℓ-α,α′-dihydroxyglutaric acid.
-
2.
The diastereomers of α,α′-dibromoglutaric acid and the d,ℓ-forms (in contrast to the meso form) of α,α′-dihydroxyglutaric acid and their esters are conformationally uniform in the case where there is no intramolecular hydrogen bond.
-
3.
The meso forms of the conformationally uniform α,α′-disubstituted glutaric acids differ from the d,ℓ-forms in the nonequivalence of the JCH spin-spin coupling constants with the protons of the CH2 group.
-
4.
Pseudoaxial preference was detected for the CO2H and CO2Me groups in trans-2-hydroxy-4-carboxy-γ-butyrolactone and its methyl ester respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
R. G. Kostyanovskii, V. P. Leshchinskaya, Yu. I. El'natanov et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 408 (1989); 2637 (1986).
C. K. Ingold, J. Chem. Soc.,119, 305 (1921).
L. Schotte, Arkiv Kemi,9, 423 (1956); W. G. Young, H. K. Hall, and S. Winstein, J. Am. Chem. Soc.,78, 4338 (1956).
H. Kiliani and O. Matthes, Chem. Ber.,40, 1238 (1907); J. U. Nef, Liebigs Ann. Chem.,376, 22 (1910).
W. Treibs and K. Michaelis, Chem. Ber.,88, 402 (1955); F. Tailly, Bull. Soc. Chim. France, 38 (1962).
B. M. Roth and H. Schaltegger, Helv. Chim. Acta,47, 1621 (1964).
F. K. Velichko, L. V. Vinogradova, R. A. Amriev, et al., Dokl. Akad. Nauk SSSR,194, 1080 (1970); F. K. Velichko, V. I. Dostovalova, L. V. Vinogradova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 734 (1978); G. K. Velichko, V. I. Dostovalova, L. V. Vinogradova, and R. Kh. Freidlina, Org. Magn. Res.,13, 442 (1980).
H. Günther, NMR Spectroscopy -An Introduction, Wiley (1980); H. B. Kagan (ed.), Determination of Configurations by Spectrometric Methods, Vol. 1, Georg. Thieme (1977), pp. 73, 76.
A. é. Aliev, I. V. Vystorop, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2879 (1987).
F. A. Bovey, High-Resolution NMR of Macromolecules [Russian translation], Khimiya, Moscow (1977), pp. 80, 195; T. Fukuroi, Y. Fujiwara, S. Fujiwara, and K. Fujii, Anal. Chem.,40, 879 (1968).
D. Plusquellec and F. Venien, Comp. Rend. Ser. C,277, 715 (1973).
C. Jaime, R. M. Ortuno, and J. Fout, J. Org. Chem.,51, 3946 (1986).
A. J. Kirby, The Anomeric Effect and Related Stereoelectronic Effects at Oxygen, Springer-Verlag, Berlin (1983); N. S. Zefirov and N. M. Shekhtman, Usp. Khim.,40, 616 (1971).
R. Freeman, Mol. Phys.,5, 499 (1962); N. M. Tsybina, T. V. Protopopova, and A. P. Skoldinov, Zh. Org. Khim.,6, No. 2, 269 (1970).
R. Fitting, Liebigs Ann. Chem.,353, 1 (1907).
Author information
Authors and Affiliations
Additional information
For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 891–901, April, 1989.
Rights and permissions
About this article
Cite this article
Kostyanovskii, R.G., Vystorop, I.V., Aliev, A.é. et al. Automatic assembly of framework structures. Russ Chem Bull 38, 801–810 (1989). https://doi.org/10.1007/BF00953295
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00953295