Abstract
The reaction of 4-dihalomethyl-4-methyl-2,5-cyclohexadien-1-ones with (Me3Si)2NNa yielded spiro[(2,3,3a,6,7, 7a-hexahydro-3, 3-dihalo-3a-methylbenzofuran-6-one)-2, 1′-(4′-dihalomethyl-4′-methyl-2′, 5′-cyclohexadienes)]. The structures of the spiro compounds were established based on the data of1H and13C NMR, UV, and IR spectroscopy and mass spectrometry. The mechanism and stereochemistry of the reaction are discussed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
B. Martel and M. Hiriart,Synthesis, 1972 201.
B. Martel and M. Hiriart,Angew. Chem., Int. Ed. Engl., 1972,11, 326.
P. Binger and A. Germer,Chem. Ber., 1981,114, 3325.
N. S. Zefirov, T. S. Kuznetsova, O. E. Eremenko, O. V. Kokoreva, G. V. Zatonsky, and B. I. Ugrak,J. Org. Chem., 1994,59, 4087.
H. Zimmerman and G. E. Keck,J. Am. Chem. Soc., 1975,97, 3527.
D. H. Hey, C. W. Rees, and F. R. Todd,J. Chem. Soc., C, 1967, 1518.
D. H. Hey, J. H. Jones, and M. J. Perkins, J. Chem. Soc., D, 1970, 1438.
D. H. Hey, J. H. Jones, and M. J. Perkins,J. Chem. Soc., Perkin Trans. 1, 1972, 1150.
E. Fattorusso, L. Minale, and G. Sodano,J. Chem. Soc., Chem. Comm., 1970, 752.
R. Moody, R. H. Thomson, E. Fattorusso, L. Minale, and G. Sodano,J. Chem. Soc., Perkin Trans., 1, 1977, 18.
I. A. McMillan, I. C. Paul, I. M. Goo, K. L. Rinehart, W. C. Krueger, and L. M. Pschgoda,Tetrahedron Lett., 1981, 39.
J. Gopichand and F. I. Schmitz,Tetrahedron Lett., 1974, 3921.
M. Rotem, S. Carmely, J. Kashman, and J. Loya,Tetrahedron, 1983,39, 667.
V. G. Kharitonov, V. A. Nikanorov, S. V. Sergeev, M. V. Salakhov, S. O. Yakushin, V. V. Mikul'shina, V. I. Rozenberg, and O. A. Reutov,Dokl. Akad. Nauk SSSR, 1991,310, 177[Dokl. Chem., 1991 (Engl. Transl.)].
W. F. Gannon and H. O. House,Org. Synth., 1960,40, 41.
V. M. Potapov, inStereokhimiya [Stereochemistry], Khimiya, Moscow, 1988, 87, 89 (in Russian).
M. Nogradi,Stereochemistry: Basic Concepts and Applications, Pergamon Press, Oxford, 1981.
A. B. Bother-By,Adv. Magn. Reson., 1965,1, 195.
E. W. Garbisch, Jr.,J. Am. Chem. Soc., 1964,86, 5561.
N. S. Zefirov, E. E. Dashevskaya, and V. A. Palyulin,Dokl. Akad. Nauk SSSR, 1987,292, 1380[Dokl. Chem., 1987 (Engl. Transl.)].
N. S. Zefirov, V. A. Palyulin, and E. E. Dashevskaya,J. Phys. Org. Chem., 1990,3, 147.
A. Yu. Zotov, V. A. Palyulin, and N. S. Zefirov,J. Chem. Inf. Comp. Sci., 1997, in press.
M. Barbier, D. U. R. Barton, M. Devys, and R. S. Topgi,Tetrahedron, 1987,43, 5031.
G. V. Gavrilova, A. A. Aleshkin, V. A. Nikanorov, D. P. Krut'ko, V. I. Rozenberg, and O. A. Reutov,Izv. Akad. Nauk, Ser. Khim., 1995, 519 [Russ. Chem. Bull., 1995,44, 502 (Engl. Transl.)].
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1015–1021, May, 1997.
Rights and permissions
About this article
Cite this article
Gavrilova, G.V., Krut'ko, D.P., Gavrilov, A.A. et al. Synthesis and stereochemistry of new spiranes containing 2,5-cyclohexadiene and 2,3,3a,6,7,7a-hexahydrobenzofuranone fragments. Russ Chem Bull 46, 975–981 (1997). https://doi.org/10.1007/BF02496130
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02496130