Conclusions
-
1.
Complexes of 2-(2-halogenoidethyl)-1-boraadamantanes with tetrahydrofuran and pyridine have been synthesized by the hydroboration-isomerization of 3-methoxy-7-(3-halogenoidpropyl)-3-borabicyclo[3.3.1]non-6-enes.
-
2.
4-Chloro-, and 2-(2-halogenoidethyl)-, and 2-(2-trimethylammoniumethyl)-1-boraadamantane ate-complexes undergo self-induced 1,3-elimination, resulting in the formation of substituted 3-borabicyclo[3.3.1]nonanes containing a cyclopropane fragment.
Similar content being viewed by others
Literature cited
M. F. Hawthorne, J. Am. Chem. Soc.,82, 1886 (1960).
P. Binger and R. Köster, Tetrahedron Lett., 156 (1961).
R. Köster, Houbeh-Weyl Methoden der Organischen Chemie. Organobor-Verbindungen III, Vol. 13C, 275 (1984).
B. M. Mikhailov and Yu. N. Bubnov, Organoboron Compounds in Organic Synthesis [in Russian], Nauka, Moscow (1977), p. 427.
Yu. N. Bubnov, M. E. Gurskii, A. I. Grandberg, and D. G. Pershin, Tetrahedron,42, 1079 (1986).
B. M. Mikhailov and M. Yu. Étinger, Izv. Akad. Nauk SSSR, Ser. Khim., 1197 (1984).
B. M. Mikhailov and K. L. Cherkasova, Izv. Akad. Nauk SSSR, Ser. Khim., 1837 (1984).
M. E. Gurskii, A. S. Shashkov, and B. M. Mikhailov, Izv. Akad. Nauk SSSR, Ser. Khim., 341 (1981).
B. M. Mikhailov and K. L. Cherkasova, J. Organomet. Chem.,246, 9 (1983).
H. L. Goering and S. L. Trenbeath, J. Am. Chem. Soc.,98, 5016 (1976).
J. A. Marshall, Synthesis, 229 (1971).
L. Brandsma, Preparative Acetylenic Chemistry, Elsevier Publishing Co., Amsterdam-London-New York (1979), p. 159.
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 415–420, February, 1988.
Rights and permissions
About this article
Cite this article
Gurskii, M.E., Potapova, T.V., Cherkasova, K.L. et al. 1,3-Elimination in γ-halogen- and γ-ammonium-1-boraadamantane ate-complexes. Russ Chem Bull 37, 334–338 (1988). https://doi.org/10.1007/BF00957439
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00957439