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分类

• {SNA} Chemical Synthesis, Protecting and Derivatizing Reagents, Protection and Derivatization, Silicon-Based, Synthetic Reagents
• {uni_hamburg} no charge; 1fragment

产品应用

• An efficient reagent for ether, ester, carbamate, ketal, and lactone cleavage

相关文献及参考

• Alkyl carbamates are cleaved to amines, via the TMS esters: J. Chem. Soc., Chem. Commun., 315 (1978); for application to cleavage of N-Cbz and N-Boc groups, see: J. Chem. Soc., Chem. Commun., 495 (1979).
• Effective reagent for the O-alkyl cleavage of carboxylic esters: J. Am. Chem. Soc., 99, 968 (1977). The reaction can be catalyzed by iodine: J. Org. Chem., 44, 2185 (1979).
• Reactive silylating agent for conversion of ketones to silyl enol ethers (see Appendix 4). In triethylamine, the rate of silyl enol ether formation by TMS iodide is 7x109 times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980). In combination with Hexamethyl­disilazane, A15139, unsymmetrical ketones give the thermodynamically more stable isomer: Synthesis, 730 (1979).
• Alcohols are converted to alkyl iodides: Tetrahedron Lett., 2659 (1977). ɑɑ-Diaryl alcohols are reduced to the corresponding alkanes: Tetrahedron, 51, 11043 (1995); Synth. Commun., 26, 101 (1996).
• Catalyzes the transesterification of esters, even those of hindered acids: Synthesis, 142 (1981).
• Short: III/20c
• Short: II/4
• For reviews of the use of iodotrimethylsilane in organic synthesis, see: Synthesis, 861 (1980); Tetrahedron, 38, 2225 (1982); Adv. Silicon Chem., 1, 1 (1991).
• Short: III/35F
• Valuable reagent for the mild cleavage of dialkyl and aralkyl ethers: J. Org. Chem., 42, 3761 (1977).
• Catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives, effective at lower temperatures than bromotrimethylsilane: Org. Lett., 5, 1661 (2003).
• Catalyst for the protection of alcohols, under mild neutral conditions, as MOM ethers by trans-acetalization with Dimethoxymethane, A12055: Synthesis, 896 (1983), and as THP ethers by acetalization with dihydropyran: Synthesis, 703 (1985).
• Beilstein: 4,IV,4009

安全信息

其他信息

• Iodotrimethylsilane is an efficient reagent for ether, ester, carbamate, ketal, and lactone cleavage.Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides. For the introduction of the TMS group, e.g., TMS enol ethers.
• 和水发生反应。