Conclusions
-
1.
The reaction of dichloro- and diiodogermulenes with 2,2,6,6-tetramethyl-4-thiacyclo-heptyne gave 80–85% yields of the Δ−1.7-2,2,6,6-tetramethyl-8,8,9,9-tetrachloro- and Δ−1.7-2,2, 6,6-tetramethyl-8,8,9,9-tetraiodo-4-thia-8,9-digermabicyclo[5.2.0]nonenes, which are the first examples of a new class of heterocyclic compounds- the 1,2-digermacyclobut-3-enes.
-
2.
The 1,1,2,2-tetrachloro(iodo)-1,2-digermacyclobut-3-enes obtained are thermally stable to 200–230°C they do not react with O2 MeOH, or HClAgF. They react comparatively readily with sulfur (with the formation of the corresponding 1-thia-2,5-digermacyclopent-3-enes) and SbCl5 (giving Δ−1.7-2,2,6,6-tetramethyl-9-oxa-4-thia-8,8,10,10-tetrachloro-8,10-digermabicyclo[5.3.0]decene after partial hydrolysis).
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
A. A. Espenbetov, Yu. T. Struchkov, S. P. Kolesnikov, and O. M. Nefedov, J. Organomet. Chem.,275, 33 (1984). S. P. Kolesnikov, A. Krebs, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2173 (1983). S. P. Kolesnikov, M. P. Egorov, A. M. Gal'minas, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 2832 (1985).
R. T. Conlin and P. P. Gaspar, J. Am. Chem. Soc.,98, 3715 (1976). D. Seyferth, D. C. Annarelli, and S. C. Vick, J. Am. Chem. Soc.,98, 6382 (1976). M. Ishikawa, T. Fuchikami, and M. Kumada, J. Am. Chem. Soc.,99, 245 (1977). H. Sakurai, Y. Kamiyama, and Y. Nakadaira, J. Am. Chem. Soc.,99, 3879 (1977).
W. H. Atwell and J. G. Ulmann, J. Organomet. Chem.,52, C21 (1973). C.-S. Liu, J. L. Margrave, and J. C. Thompson, Can. J. Chem.,50, 465 (1972).
A. Krebs and J. Berndt, Tetrahedron Lett.,24, 4083 (1983). M. P. Egorov, S. P. Kolesnikov, Yu. T. Struchkov, et al., J. Organomet. Chem.,290, C27 (1985). M. P. Egorov, S. P. Kolesnikov, Yu. T. Struchkov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 959 (1985).
O. M. Nefedov, S. P. Kolesnikov, M. P. Egorov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 2834 (1985).
S. P. Kolesnikov, I. S. Rogozhin, and O. M. Nefedov, Izv. Akad. Nauk SSSR, Ser. Khim., 2379 (1974).
A. Krebs and H. Kimling, Tetrahedron Lett., 761 (1970).
M. E. Vol'pin, V. G. Dulova, Yu. T. Struchkov, et al., J. Organomet. Chem.,8, 87 (1967).
L. E. L. Sutton, Tables of Interatomic Distances and Configuration in Molecules and Ions: Spec. Publication No. 18, Chem. Soc. (1958).
E. Coldish, K. Hedberg, and V. Schomaker, J. Am. Chem. Soc.,78, 2714 (1956).
J. Donohue, The Structures of the Elements, Wiley, New York (1974).
M. Drager and L. Ross, Z. Anorg. Allg. Chem.,460, 207 (1980).
A. Krebs and J. Wilke, Top. Curr. Chem.,109, 189 (1983).
V. M. Shostakcvskii, V. L. Zlatkina, A. E. Vasil'vitskii, and O. M. Nefedov, Izv. Akad, Nauk SSSR, Ser. Khim., 2126 (1982).
E. L. Muetterties, Inorg. Chem.,1, 342 (1962).
T. G. Oikova and G. G. Gospodinov, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol.,23, 1331 (1980).
R. Danico, J. Org. Chem.,29, 1971 (1964).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1835–1840, August, 1987.
Rights and permissions
About this article
Cite this article
Kolesnikov, S.P., Egorov, M.P., Gal'minas, A.M. et al. Synthesis, structure, and properties of derivatives of 1,1,2,2-tetrahaloid-1,2-digermacyclobut-3-enes -the first examples of a new class of heterocycles. Russ Chem Bull 36, 1701–1707 (1987). https://doi.org/10.1007/BF00960138
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00960138