F Iodotrimethylsilane

As with other non-metal derivatives, reactivity depends on chain-length, branching and degree of halogen substitution. Individually indexed compounds are f Chloromethylphenylsilane, 2810 f Chlorotrimethylsilane, 1304 f Cyanotrimethylsilane, 1665 f Dichlorodiethylsilane, 1683 f Dichlorodimethylsilane, 0902 f Dichloroethylsilane, 0903 f Dichloromethylsilane, 0470 f Dichloromethylvinylsilane, 1208 f Iodotrimethylsilane, 1306 f Methyltrichlorosilane, 0439 f Trichloroethylsilane, 0854 f Trichlorovinylsilane, 0746... 

Iodosovinyl chloride, 0687 Iodosylbenzene, 2245 Iodosylbenzene tetrafluoroborate, 2288 4-Iodosyltoluene, 2749 4-Iodotoluene, 2746 f Iodotrimethylsilane, 1302 4-Iodylanisole, 2751 Iodylbenzene, 2246 2-Iodylbenzoic acid, 2677 4-Iodyltoluene, 2750 2-Iodylvinyl chloride, 0688 Nitrogen triiodide—ammonia, 4630 Nitrogen triiodide—silver amide, 4629 Nitrogen triodide, 4628 Orthoperiodic acid, 4537... 

Trimethylsilyl l//-azepine-f-carboxylate (4), prepared in 71 % yield by treating methyl 17/-azepine-1 -carboxylate with iodotrimethylsilane in chloroform at 20°C, with methanol in pentane solution at — 78 °C undergoes slow hydrolysis to the bright-yellow 17/-azepine-l-carboxylic acid (5),9 which is also obtained, as the potassium salt, by the action of potassium /ert-butoxide on ethyl 17/-azepine-l-carboxylate.139 The acid is stable at —78°C for several days but in chloroform solution at 20 °C undergoes decarboxylation to 17/-azepine (6) accompanied by some decomposition. 17/-Azepine is stable for a few hours at — 78 C and has been characterized by 3H and l3CNMR spectroscopy. 

Oxiranes react with iodotrimethylsilane to give silylated halo alcohols e.g. 60) which can be converted to allylic alcohols (Scheme 53) (80JOC2579, 80TL2329) cf. other syntheses of allylic alcohols (Sections 5.05.3.2.2, 5.05.3.4.3(f) and (w)). 

Iodomethyltrimethylsilane, 315 Iodotrimethylsilane, 329 Ketene alkyl trialkylsilyl acetals or ke-tals, 19, 237, 306, 307, 351 Ketene f-butyl t-butyldimethylsilyl acetal, 237... 

Halosilanes are also potent halogen donors, particularly in exchange reactions with alkyl fluorides, due to the strong Si-F bond formation. Tertiary- and secondary-alkyl fluorides are reacted with iodotrimethylsilane to yield alkyl iodides in high yields (equation 19)214 ... 

Scheme 10.63. A representation of the formation and some of the uses of iodotrimethylsilane [(CH3)3SiI]. See Pray, B. O. Sommer, L. H. Goldberg, G. M. Kerr, G. T. Di Giorgio, P. A. Whitmore, F.C.J.Am. Chem. Soc., 1948,70,433 Fleming, I. Dunogues, J. Smithers, R. Organic Reactions, Vol. 37, Kende, A. S., ed. Wiley, Hoboken, NJ, 1989.

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