Abstract
1-(2-Furyl)-3-amino-4,4-dimethylpentane was used to obtain 3-tert-butyl-1,2-dihydropyrrolizine, the catalytic hydrogenation of which over Rh/Al2O3 at room temperature gives a mixture of cis- and trans-3,8-H-3-ter-butylpyrrolizidines with predominance of the cis isomer, whereas hydrogenation at 90–100 °C gives a mixture containing the trans isomer as the principal component. The three-dimensional structures of the isomers follow from data on the catalytic hydrogenation and isomerization and the IR, Raman, and PME spectra. A considerable percentage of the trans-fused form is characteristic for cis-3,8-H-3-tert-butylpyrrolizidine.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
I. M. Skvortsov and V. M. Levin, Khim. Geterotsikl. Soedin., 947 (1973).
I. M. Skvortsov and J. A. Elvidge, J. Chem. Soc., B, 1589 (1968).
I. M. Skvortsov, V. V. Tarasov, I. V. Antipova, V. M. Levin, S. A. Kolesnikov, and I. Ya. Evtushenko, in: Material from the First All-Union Conference on Dynamic Stereochemistry and Conformational Analysis [in Russian], Odessa (1970), p. 94.
K. Venter, S. Giller, and A. Lazdyn'sh, Izv. Akad. Nauk Latv. SSR, No. 5, 87 (1961).
A. A. Ponomarev, N. P. Maslennikova, and A. P. Kriven'ko, Zh. Obshch. Khim., 31, 958 (1961).
R. P. Linstead, W. E. Doering, S. B. Davis, P. Levine, and R. R. Whestone, J. Amer. Chem. Soc., 64, 1985 (1942).
I. M. Skvortsov, and I. V. Antipova, in: Heterogeneous Catalysis in Reactions for the Preparation and Transformation of Heterocyclic Compounds [in Russian], Zinatne, Riga (1971), p. 123.
I. Tabushi, K. Fujita, and R. Oda, J. Org. Chem., 35, 2383 (1970).
K. Fujita, K. Hata, R. Oda, and I. Tabushi, J. Org. Chem., 38, 2640 (1973).
S. Winstein, P. Carter, F. A. L. Anet, and A. J. R. Bourn, J. Amer. Chem. Soc., 87, 5247 (1965).
B. V. Cheney, J. Amer. Chem. Soc., 90, 5386 (1968).
H. P. Hamlow, S. Okuda, and N. Nakagawa, Tetrahedron Lett., 2553 (1964).
F. Bohlmann, D. Schumann, and C. Arndt, Tetrahedron Lett., 2705 (1965).
F. Bohlmann, D. Schumann, and H. Schulz, Tetrahedron Lett., 173 (1965).
R. Granger, L. Bardet, C. Sablayrolles, and J. P. Girard, Bull. Soc. Chim. France, 391 (1971).
R. Granger, L. Bardet, C. Sablayrolles, and J. P. Girard, Bull. Soc., Chim. France, 4454 (1971).
Tran Suan Khoan', Master's Dissertation [in Russian], Moscow (1973).
Organic Syntheses, [Russian translation], Vol. 3 (1952), p. 338.
A. A. Ponomarev, V. A. Sedavkina, and Z. V. Til', Zh. Obshch. Khim., 33, 1303 (1963).
A. A. Ponomarev and I. M. Skvortsov, in: Methods for the Preparation of Reagents and Compounds [in Russian], No. 17, IREA, Moscow (1967), p. 65.
Yu. K. Yur'ev and P. M. Rakitin, Zh. Obshch. Khim., 7, 485 (1937).
S. A. Kolesnikov, Master's Dissertation [in Russian], Saratov (1972), p. 171.
Author information
Authors and Affiliations
Additional information
See [1] for communication XI.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1087–1095, August, 1975.
Rights and permissions
About this article
Cite this article
Skvortsov, I.M., Antipova, I.V., Pentin, Y.A. et al. Research on 1-azabicyclic compounds. Chem Heterocycl Compd 11, 949–955 (1975). https://doi.org/10.1007/BF00470497
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00470497