Abstract
Reactions of organo(trichloromcthyl)silanes RMc2SiCCl3 (R = Me, Ph, Mc3Si) with aluminum chloride have been studied. The interaction of trimetltyl(tricltlorometltyl)silane with AlCl3 carried out in cyclohexane or in benzene leads to Me3SiCHCI2 (in 75 % yield) or ClMe2SiCPh2Me (in 70 % yield), respectively; whereas no conversions are observed inn-hexane and methylene chloride. Treatment of dimetltyl(phenyl)(ricltloromethyl)silane with aluminum chloride in an-C5H12/CH2CI2 mixture gives an aromatic cross-linked insoluble polymer. The reaction of pentamethyl(trichloromcthyl)disilane (R = Mc3Si) with AICl3 in pentane affords the rearrangement product, Me3SiCCl2SiMc2Cl, in 65 % yield. In methylene chloride the further cleavage of the disilane occurs to yield Me2SiCl2 and CH2=CHMe2SiCl.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. V. Motsarev, M. V. Sobolevskii, V. R. Rosenberg,Karbofunktsional nye organosilany i organosiloksany [Carbofunctional Organosilones arid Organosiloxanes], Khitmiya, Moscow, 1990 (in Russian).
R. Anderson,Synthesis, 1985,8, 717.
A. N. Kornev, V. V. Semenov., O. C. Donnikova, and Yu. A. Kurskii,Izv. Akad. Nauk, Ser. Khim., 1995, 150 [Russ. Chem. Bull., 1995,44, 145 (Engl. Transl.)].
K. A. Petrov, V. A. Chausov, I. V. Pastukhova, and N. V. Pakhitnova,Zh. Obshch Khim., 1978,48, 1377 [J. Appl. Chem. USSR, 1978,48 (Engl. Transl.)].
T. J. Hairston and D. H. O'Brien,J. Organomet. Chem., 1971,29, 79.
K. Tamao and M. Kutnada,J. Organomet. Chem., 1971,30, 339.
M. Kumada and M. Jshikava,J. Orgariomet. Chem., 1964,1, 411.
M. Ktunada, I.-I. Nakajima, M. Ishikava, and Y. Yamamoto,J. Org. Chem., 1958,23, 291
L. H. Sommer, D. L. Bailey, J. R. Gould, and F. C. Whitmore,J. Am. Chem. Soc., 1954,76, 801.
Metody elementoorganicheskoi khimii: khlor. Alifaticheskiye soedineniya [Methods of Organoelement Compounds: Chlorine, Aliphatic Compounds], Ed. by A. N. Nesmeyanov and K. A. Kocheshkov, Nauka, Moscow, 1973 (in Russian).
R. A. Benkeser and W. E. Smith,J. Am. Chem. Soc., 1968,90, 5307.
V. S. Romanova, Z. N. Parries, and P. I. E. Vol'pin,VII Vsesoyuzn. konf, po khimii, tekhnologii proizvodstva i prakticheskomu primeneniyu kremneorganicheskikh soedinenii [VII All-Union Conf. on Chemistry, Production Technology and Applications of Organosilicon Compounds], Thilisi, 1990, part I, 104 (in Russian).
V. I. Zhun, O. L. Ustinova, V. D. Sheludyakov, G. N. Turkel'taub, T. F. Slyusarenko, S. N. Tandura, and S. I. Androsenko,Zh. Obshch. Khim., 1990,60, 1111 [J. Appl. Chem. USSR, 1990,60 (Engl. Transl.)].
R. W. Bott, C. Eaborn, and B. M. Rushton,J. Organomet. Chem., 1965,3, 455.
C. Eaborn, A. R. Hancock, and W. A. Stanczyk,J. Orgariomet. Chem., 1981,218, 147.
Organometallic Compounds of Silicon, Ed. by D. R. M. Walton, London, New York, 1985, 48.
D. R. Dimel, C. A. Wilke, and F. Ramon,J. Org. Chem., 1972,37, 2662.
G. Fritz, and W. Himmes,Z Anorg. Allg. Chem., 1979,448, 55
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1511-1515, June, 1996.
Rights and permissions
About this article
Cite this article
Kornev, A.N., Semenov, V.V. & Kurskii, Y.A. AlCl3-Catalyzed transformations of organo(trichloromethyl) silanes. Russ Chem Bull 45, 1440–1444 (1996). https://doi.org/10.1007/BF01434229
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF01434229