Summary
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1.
The dehydrochlorination of the following compounds was carried out for the first times With the aid of quinolines Cl2SiCH2CHClCH2, Cl2SiCH2CCl(CH2)2 and Cl2SiCHClCH2SiCl2. With the aid of aluminum chloride: 1,1- 1,2- and 2,2-dichloroethyltrichlorosilanes, Cl2SiCH2CH (CH2)CH2Cl and Cl2SiCHClCH2SiCl2.
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2.
It was shown that, when quinolines was used, dehydrochlorination products were obtained in high yield only when the chlorine atom was in the\gb-position with respect to silicon, the products being exclusively 1-alkenylsilanes. Aluminum chloride can be applied for dehydrochlorination only in the case of trichlorochloroalkyl)silanes, but the chlorine atom may be in the\ga-,\gb-, or\gg-position.
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3.
A new arrangement in organosilicon chemistry was discovered.
In the dehydrochlorination of 1-chloro-1,2-bistrichlorosillylethane (1,1,2,4,4,4-heptachloro-1,4-disilabutane) with quinoline, only 1,2-bistrichlorosilylethylene was formed, whereas in dehydrochlorination with aluminum chloride the same product was obtained in admixture with 1,1-bistrichlorosilylethylene. A scheme is given in which an isomeric change in the skeleton of the original compound occurs in the course of the dehydrochlorination.
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Literature cited
S. N. Ushakov and A. M. Itenberg, J. Gen. Chem. 7, 2495 (1937).
D. T. Hurd, J. Am. Chem. Soc, 67, 1813 (1945).
G. H. Wagner, D. L. Bailey, and A. N. Pines, Ind. Eng. Chem. 45, 367 (1953).
L. H. Sommer, D. L. Bailey, and F. C. Whitmore, J. Am. Chem. Soc. 70, 2869 (1948).
D. L. Bailey and A. N. Pines, Ind. Eng. Chem. 46, No. 11, 2363 (1954).
L. H. Sommer, D. L. Bailey, J. R. Gould and F. C. Whitmore, J. Am. Chem. Soc. 76, 801 (1954).
L. H. Sommer, R. E. Van Strien and F. C. Whitmore, J. Am. Chem. Soc. 71, 3056 (1949).
L. H. Sommer, D. L. Bailey, G. M. Goldberg, C. F. Buck, T. S. Bye, F. J. Evans and F. C. Whitmore, J. Am. Chem. Soc. 76, 1613 (1954).
C. L. Agre and W. Hilling, J. Am. Chem. Soc. 74, 3895 (1952).
A. V. Topchiev, N. S. Nametkin, and A. A. Shcherbakova, Proc. Acad. Sci. USSR 86, No. 3, 359 (1952).
A. D. Petrov and L. L. Shchukovskaya, Proc. Acad. Sci. USSR 86, No. 3, 331 (1952).
L. H. Sommer, G. M. Goldberg, E. Dorfman and F. C. Whitmore, J. Am. Chem. Soc. 68, 1083 (1946).
K. A. Kocheshkov, I. F. Lutsenko, and O. A. Reutov, Prog. Chem. 18, 497 (1949); A. N. Nesmeyanov, R. Kh. Freidlina, and A. J. Kochetkov, Bull. Acad. Sci. USSR, Div. Chem. 1948, 29.
V. A. Ponomarenko and V. F. Mironov, Proc. Acad. Sci. USSR 94, No. 3 485 (1954).
A. D. Petrov, V. F. Mironov, V. A. Ponomarenko, and E. A. Chernyshev, Proc. Acad. Sci. USSR 97, No. 4 687 (1954).
V. F. Mironov, V. G. Glukhovtsev, and A. D. Petrov, Proc. Acad. Sci. USSR 104, No. 6, 865 (1955).
V. F. Mironov and N. A. Pogonkina, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1953, 182 (T.p. 161).
A. D. Petrov and V. F. Mironov, Proc. Acad. Sci. USSR 80, 761 (1951).
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Petrov, A.D., Mironov, V.F. & Mashantaker, D. Dehydrochlorination of trichloro(chloroalkyl)- and trichloro(dichloroalkyl)-silanes. Rearrangement of 1,1,1,2,4,4,4-heptachloro-1,4-dislabutane during dehydrochlorination with aluminum chloride. Russ Chem Bull 5, 547–555 (1956). https://doi.org/10.1007/BF01169301
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DOI: https://doi.org/10.1007/BF01169301