Abstract
Dehydrobromination of 10,10-dimethyl-9-(2,3-dibromoprop-1-y1)-9,10-dihydro-10-sila-2-aza-9-anthrol with butyllithium follows two routes to give the Z- and E-isomers of furan ring-brominated spiro(dihydrosilaazaanthracene-9,2′-tetrahydrofuran), and the cis- and trans-isomers of 10,10-dimethyl-9-(3-bromoallyl)-9,10-dihydro-10-sila-2-aza-9-anthrol. Analogous compounds have been obtained bearing an azidogroup in the tetrahydrofuran ring, and a spiran with a dihydrofuran fragment. The pure isomers have been isolated, and their structures established.
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O. A. D'yachenko, L. O. Atovmyan, S. Soboleva, T. Yu. Markova, N. G. Komalenkova, L. N. Shamshin, and E. A. Chernyshev, Khim. Skh. Khim., 15, 170 (1974).
O. A. Dyachenko, Y. A. Sokolova, L. O. Atovmyan, A. N. Chekhlov, N. S. Prostakov, A. V. Varlamov, and N. Saxene (Saksena), J. Organomet. Chem., 209, 147 (1981).
L. M. Rice, B. S. Sheth, and J. W. Wheeler, J. Heterocycl. Chem., 10, 731, 737 (1973).
N. S. Prostakov, N. Saksena, A. V. Varlamov, and A. M. Klochkov, Khim. Geterotsikl. Soedin., No. 2, 240 (1982).
R. S. Cooksen, T. A. Crabb, J. J. Frankel, and J. Hudec, Tetrahedron, 355 (1966).
J. Jeener, B. H. Meier, P. Bachmann, and R. R. Ernst., J. Chem. Phys., 71, 4645 (1979).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 696–700, May, 1989.
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Prostakov, N.S., Varlamov, A.V., Kozm, K. et al. 4′-Bromo(and azido)-10,10-dimethylspiro[9,10-dihydro-10-sila-2-azaanthracene-9,2′-tetrahydrofuran]. Chem Heterocycl Compd 25, 581–585 (1989). https://doi.org/10.1007/BF00482514
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DOI: https://doi.org/10.1007/BF00482514