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The use of a separately prepared sodium alkyl in this way provides the same degree of control as in a Grignard synthesis, and the reactions indeed action ensues. are very similar. in the same way. Organolithium compounds probably could be used When Victhe the of separate preparation Grignard developed organomagnesium halides as reagents, he not only opened a wide field of 3. SUBSTITUTION BY ORGANOMAGNESIUM COMPOUNDS. tor first synthesis in organic chemistry but also gave a great impetus to organosilicon chemistry.

Patent 2 238 669 to R. H. Wiley. ^Soshestvenskaya, J. Gen. Chem. USSR 8, 294 (1938); ibid. 10, 1689 (1940); Manulkin and Yakubova, J. Gen. Chem. USSR 10, 1300 (1940). 31 Kipping and Blackburn, /. Chem. Soc. 1932, 2200. 82 Polis, Ber. 18, 1540 (1885). 33 Kipping and Lloyd, /. Chem. Soc. 79, 449 (1901). 34 Smith and Kipping, J. Chem. Soc. 101, 2553 (1912). ; THE ORGANOSILICON MONOMEK8 32 (as in the preparation of tripropylallylsilane from silicon tetrapropyl), but most have been made by the successive replacement of the chlorine in silicon tetrachloride with different radicals supplied by Grignard reagents, as in these examples: + C 6H 5 MgBr = C 6H 5SiCl3 + MgBrCl C 6H 5SiCl3 + C 2 H 5 MgBr = (C 6 H 5 (C 2 H 6 )SiCl 2 + MgBrCl (C 6H 5 )(C 2H 5 )SiCl 2 + C 3 H 7 MgBr = (C 6H 5 )(C 2 H 6 )(C 3 H 7 )SiCl + MgBrCl (C 6H 5 )(C 2 H 5 )(C 3 H 7 )SiCl + CH 3 MgBr = (C 6H 5 )(C 2 H 5 )(C 3 H 7 )(CH 3 )Si + MgBrCl SiCU ) A mixed alkyls, together with their physical propmethods of preparation, and literature references, is given in 35 Those with four different groups represent Krause and von Grpsse.

16 Hyde and DeLong, J. Am. Chem. Soc. 63, 1194 (1941). "Kipping, /. Chem. Soc. 101, 2125 (1912). * See Chapter 1. SILOXANE NETWORKS 53 SILOXANE NETWORKS Whether in cyclic form or in straight chains terminated by hydroxyl or trimethylsilyl groups, the organosiloxane polymers so far considered have consisted principally of repetitions of the unit SiO R2 Now necessary to consider another concept, that of the cross linking of siloxane chains and rings. Cross linking is a means of further increasthe molecular average ing weight of the polymer, and at the same time it is it also serves to establish a three-dimeasional rigidity and decreased One way network of increased solubility.

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