Di-i-propylphenyltrimethylsilane .--The bromide was coupled with trimethylchlorosilane by sodium according to the Drocedure emnloved for the diethvl comnound. The product, which &as "fractionated thro;gh a Todd column, boiled a t 94-95" ( t m m . ) , 1 2 2 0~ 1.4894, d2O1 1.8605; ildR found 78.60, JBR calcd. (7.90.Anal. Calcd. for ClsH2&i: C , 76.84; 13, 11.18. Found: C, 76.54; H, 11.00 3,5-Di-t-butyltoluene42 was prepared in 46y0 yield. The product, which was fractionated through a Todd column, boiled a t 94.595' (5 mm. (reported42 b.p. 98" (6 mm.).3,s-Di-l-butylbenzoic d~id.~~--Oxidation of the di-tbutyltoluene gave the desired acid in 6472 yield, m.p. 170-171.5" (lit.43m.p. 172').3,5-Di-t-butylaniline. 44-X Schmidt reaction on the acid gave the amine (m.p. 52.5-54') in 8870 yield (lit.44 m. p . 50.5-53").
3,s-Di-t-butyliodobenzenewas prepared in 33y0 yield according to the procedure described in the 1iterat~re.d~ The iodide melted a t 66-67' (lit.44 m.p. 67-68'). 3,5-Di-t-butylphenyltrimethylsilane .--A solution of 25.25 g . (0.08 mole) of 3,5-di-t-butyliodobenzene in 75 ml. of ether (42) J . Greuze, C. Ruinard, J . Soetcrbroek, P. E. Verkade and B 11.(43) W. VanHartingsveldt, P. E. Verkade a n d U RL \Vepster, ibid.
Tertiäre Alkylhalogenide (I) werden durch Behandlung mit Natriumboranat in Sulfolan unter Annahme der Zwischenstufen (II) und (III) in einer Stufe zu den Kohlenwasserstoffen (IV) dehalogeniert.
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