Conclusions
-
1.
When 1-silacyclopentanes, containing chloromethyl radicals attached to the silicon atom, are treated with nucleophilic reagents the reaction does not proceed by the nucleophilic substitution scheme, as is the case for compounds of type R3SiCH2Cl, but instead the reaction of expansion of the silicocarbon skeleton, specific for silacycloalkanes, is observed, with the formation of the next member of the homologous series.
-
2.
In this connection the formation of noticeable amounts of the cleavage products of the chloromethyl group was not detected.
-
3.
The discovered reaction has preparative interest for obtaining alkoxy and siloxane derivatives of monosilacyclohexanes.
Similar content being viewed by others
Literature cited
V. M. Vdovin, N. S. Nametkin, K. S. Pushchevaya, and A. V. Topchiev, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk,1963, 274.
V. M. Vdovin, N. S. Nametkin, V. I. Zav'yalov, and K. S. Pushchevaya, J. Prakt. Chem.,23, 281 (1964).
K. S. Pushchevaya, Dissertation [in Russian], Moscow (1967).
N. S. Nametkin, V. M. Vdovin, and K. S. Pushchevaya, Izv. Akad. Nauk SSSR, Ser. Khim.,1967, 2537.
F. C. Whitmore, L. H. Sommer, and J. Gold., J. Am. Chem. Soc.,69, 1976 (1947)
M. Kumada, M. Ishikawa, and K. Tamao, J. Organometal. Chem.,5, 226 (1966).
N. S. Nametkin, V. M. Vdovin, E. D. Babich, and T. N. Arkhipova, Dokl. Akad. Nauk SSSR,171, 1345 (1966).
N. S. Nametkin, V. D. Oppengeim, V. I. Zav'yalov, K. S. Pushchevaya, and V. M. Vdovin, Izv. Akad. Nauk SSSR. Otd. Khim. Nauk,1965, 1547.
J. Speier, J. Am. Chem. Soc.,70, 4142 (1948).
R. W. Bott, C. Eaborn, and T. W. Swaddle, J. Organometal. Chem.,5, 233 (1966).
R. West, J. Am. Chem. Soc.,76, 6012 (1954).
F. J. Bajer and H. W. Post, J. Org. Chem.28, 1941 (1963).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 836–839, April, 1968.
Rights and permissions
About this article
Cite this article
Nametkin, N.S., Babich, E.D., Arkhipova, T.N. et al. Reaction for expansion of silicocarbon heterocycles under the influence of nucleophilic reagents. Russ Chem Bull 17, 800–802 (1968). https://doi.org/10.1007/BF00905757
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00905757