The mechanism for cleavage of esters is described in PNAS, 75(1), 4-6 (1978).The authors go on to explain that the data do not support a previously published mechanism via a carbenium iodide.The paper also discusses the cleavage of ethers using iodotrimethylsilane. It appears that this is not as efficient as cleavage of esters, and a couple of mechanisms (pages 5 and 6) are proposed.Olah also described the cleavage of the phosphate esters in peptides that contain phosphate esters, using iodotrimethylsilane (Tetrahedron, 38, 2225 (1982)). The amide linkages in the peptide backbone are not cleaved.
748854
Iodotrimethylsilane solution
1 M in dichloromethane
Synonym(e):
Iodotrimethylsilane solution, TMS iodine, TMS-I, TMSI, Trimethyliodosilane
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100 ML
CHF 391.00
About This Item
Empirische Formel (Hill-System):
C3H9ISi
Molekulargewicht:
200.09
UNSPSC-Code:
12352101
NACRES:
NA.22
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Form
liquid
Qualitätsniveau
Konzentration
1 M in dichloromethane
Brechungsindex
n20/D 1.433
Dichte
1.334 g/mL at 25 °C
Lagertemp.
2-8°C
Verwandte Kategorien
Allgemeine Beschreibung
Iodotrimethylsilane [(CH3)3SiI] is an important and versatile organosilicon reagent with wide applications in organic synthesis. It is used as a neutral nucleophilic reagent, trimethylsilylating agent, Lewis acid catalyst, reducing agent and dehydrating agent in many organic reactions.[1]
Signalwort
Danger
H-Sätze
Gefahreneinstufungen
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
Zielorgane
Central nervous system
Zusätzliche Gefahrenhinweise
Lagerklassenschlüssel
3 - Flammable liquids
WGK
WGK 3
Flammpunkt (°F)
-23.8 °F
Flammpunkt (°C)
-31 °C
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One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 53(28), 3585-3589 (2012)
Regio-and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 54(10), 1309-1311 (2013)
Iodotrimethylsilane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2005)
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