Summary
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1.
In presence of Speier's catalyst dichloromethylsilane adds to piperylene in the 1,4-positions with formation of dichloromethyl (1-methyl-2-butenyl)silane.
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2.
The addition of CH3SiCl2H to various monosubstituted derivatives of acetylene proceeds in such a way that the silyl group adds exclusively to the hydrogenated carbon atom participating in the triple bond.
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Literature cited
D. J. Bailey and A. N. Pines, Ind. Eng. Chem.46, 2363 (1954).
A. J. Barry, L. De Pree, I. W. Gilkey, and D. E. Hook, J. Am. Chem. Soc.69, 2916 (1947); U. S. Patent 2,626,271 (1953).
A. D. Petrov, V. A. Ponomarenko, B. A. Sokolov, and G. V. Odabashyan, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk,1206 (1957).
L. A. Goldblatt and D. M. Oldroyd, U. S. Patent 2,533,240 (1950); C. A.45, 2262 (1951).
R. D. Lipscomb, U. S. Patent 2,570,462 (1951); C. A.46, 6141 (1952).
G. H. Wagner, U. S. Patent 2,637,738 (1953); C. A.48, 8254 (1954).
J. L. Speier, J. A. Webster, and G. H. Barnes, J. Am. Chem. Soc.79, 976 (1957).
J. L. Speier, R. Zimmerman, and J. Webster, J. Am. Chem. Soc.78, 2279 (1956).
J. L. Speier, J. A. Webster, and G. H. Barnes, J. Am. Chem. Soc.79, 974 (1957).
F. Mackenzie, L. Spialter, and N. Schofman, British Patent 684,579; C. A.48, 2761 (1954).
C. A. Burkhard, J. Am. Chem. Soc.72, 1402 (1950).
R. A. Benkeser and R. A. Hickner, J. Am. Chem. Soc.80, 5298 (1958).
A. D. Petrov and S. I. Sadykh-Zade, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 513 (1958).
L. L. Shchukovskaya, A. D. Petrov, and Yu. P. Egorov, Zhur. Obshchei Khim.26, 3338 (1956).
A. D. Petrov, L. L. Shchukovskaya, S. I. Sadykh-Zade, and Yu. P. Egorov, Doklady Akad. Nauk SSSR115, 522 (1957).
C. L. Agre, J. Am. Chem. Soc.71, 300 (1949).
A. D. Petrov, V. F. Mironov, and V. G. Glukhovtsev, Zhur. Obshchei Khim.27, 1535 (1957).
L. H. Sommer and D. L. Bailey, J. Am. Chem. Soc.76, 1613 (1954).
V. F. Mironov and G. I. Nikishin, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 1080 (1958).
Yu. P. Egorov, L. A. Leites, and V. F. Mironov, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 510 (1958).
V. F. Mironov, Chemistry and Practical Application of Organosilicon Compounds No. 1 [in Russian] (Leningrad, 1958) p. 129.
A. N. Pudovik and N. B. Sharopova, Zhur. Obshchei Khim.25, 589 (1955).
L. L. Shchukovskaya and A. D. Petrov, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk, 1011 (1958).
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Mironov, V.F., Nepomnina, V.V. Synthesis of alkenylsilanes by the addition of dichloromethylsilane to dienic and acetylenic compounds. Russ Chem Bull 9, 1318–1322 (1960). https://doi.org/10.1007/BF00907662
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DOI: https://doi.org/10.1007/BF00907662