Iodo trimethylsilane

Silyl enol ethers.1 Aldehydes, ketones, ot,p-enals, and a,p-enones are converted into the silyl enol ethers in moderate to high yield by reaction with iodo-trimethylsilane, generated in situ, and N(C2H5)3 at 25° in acetonitrile. In some cases intermediate stable 1,2- or 1,4- adducts can be isolated. Thus the 1,2-adduct a hag been isolated as an intermediate in the reaction of some aldehydes and shown to decompose to the silyl enol ether. 

The use of alcohol 46 is attractive as it avoids a preliminary silylation step. The second equivalent of allylsilane 1 is consumed whilst generating the catalyst (iodo-trimethylsilane) and is liberated in the form of propene 48. A year later, Seebach and Imwinkelried [21] employed dialkoxydichlorotitanium complex 49 instead of... 

Benzyl-pyrazole 1-oxides 209 were debenzylated when heated with iodo-trimethylsilane and 2,6-dimethylpyridine at 70°C for 14h (1996ACSA549) (Scheme 59). 

Whereas methyl 2-siloxycyclopropanecarboxylates are thermally stable up to temperatures as high as 170 °C, they readily rearrange at low temperatures under the influence of appropriate Lewis acids. Catalytic amounts (0.05-0.4 equiv.) of iodo-trimethylsilane within minutes to days promote a quantitative ring opening of cyclopropanes 755 to the corresponding silyl enol ethers 156 (Eq. 68, Table 4)88). 

An asymmetric synthesis of the dihydrobenzo[, ]furan segment of epheradine C has been achieved by an iodo-trimethylsilane-mediated debenzylation-benzylic etherification (Equation 133) <2000J(P1)893>. 

Hosomi, A., lijima, S., and Sakurai, H., A novel aminomethylation of silyl enol ethers with aminomethyl ethers catalyzed by iodo-trimethylsilane or uimethylsilyl trifluorome-thane sulfonate. Tetrahedron I tt.. 23, 547, 1982. 

Blackburn. G.M., and Ingleson, I), fhe dealkylation of phosphate and phosphonate esters by iodo-trimethylsilane. A mild and selective procedure,, 7. Chem. Soc.. Perkin Trans. 1, 1150, 1980. 

Several new methods for the reduction of sulphoxides to sulphides have appeared. Trifluoroacetic anhydride has been used in conjunction with dimethyl sulphide, hydrogen sulphide, " or sodium iodide. The silicon compounds bromo- and iodo-trimethylsilane, or the phenyltrimethylsilane-iodine combina-... 

Such a mechanism receives support from the observation that aryl alkyl ethers are readily cleaved by the PhSiMe3-l2 reagent but only inefficiently by iodo-trimethylsilane. 

Scheme 10. Total synthesis of artemisinin by Schmid and Hofheinz. Conditions (i) ClCH20Me, PhN(CH3)2, DCM, rt. (ii) B2H6/THF, H2O2 (iii) PhCHzBr, KH, THF/DMF (iv) HCl, MeOH (v) PCC, DCM, rt. (vi) LDA, (E)-(3-iodo-l-methyl-l-propenyl)-trimethylsilane (vii) lithium methoxy(trimethylsily)methyhde (viii) Li/NH3 (ix) PCC DCM (x) m-CPBA, DCM (xi) -Bu4NF, THF, rt. (xii) O2 (methylene blue, DCM, rt.) (xiii) HCOOH, DCM.

Catalytic amounts of either t-butyl-lithium or lithium aluminium hydride induce smooth isomerization of E-(l-iodo-l-alkenyl)trimethylsilanes, via (1-lithio-l-alkenyl)silane intermediates, into the corresponding Z-isomers which show >97% isomeric purity. ... 

Alternate Name (3-iodo-1-methyl-l-propenyl)trimethylsilane. 

Iodo-l-methyl-propenyl)-trimethylsilane (Stork-Jung Vinylsilane)... 

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