Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Trimethylsilyl cyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to a trimethylsilyl group. The molecule is used in organic synthesis as the equivalent of hydrogen cyanide. It is prepared by the reaction of lithium cyanide and trimethylsilyl chloride:[1][2]
LiCN + (CH3)3SiCl → (CH3)3SiCN + LiCl
^Livinghouse, T. (1981). "Trimethylsilyl Cyanide: Cyanosilation of p-Benzoquinone". Organic Syntheses. 60: 126. doi:10.15227/orgsyn.060.0126.
^Groutas, William C.; Jin, Zhendong; Zhang, Heng (2011). "Cyanotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rc276.pub2. ISBN 978-0471936237.
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Trimethylsilylcyanide is the chemical compound with the formula (CH3)3SiCN. This volatile liquid consists of a cyanide group, that is CN, attached to...
release cyanide ions, and so have low toxicities. By contrast, compounds such as trimethylsilylcyanide (CH3)3SiCN readily release HCN or the cyanide ion...
do not exist in chemical equilibrium, unlike its silicon analog trimethylsilylcyanide. "Pivalonitrile | C5H9N | ChemSpider". www.chemspider.com. Retrieved...
of alkenes. O-Silyl cyanohydrins are generated by the addition trimethylsilylcyanide in the presence of a catalyst (silylcyanation). Cyanohydrins are...
favor of the reaction products. The cyanide source can be potassium cyanide, sodium cyanide or trimethylsilylcyanide. With aromatic aldehydes such as benzaldehyde...
and ammonium cyanide. The pure compound was produced in 2001 by the reaction of lithium tetrachloroaluminate and trimethylsilylcyanide in diethyl ether...
then reacted with an excess of trimethylsilylcyanide in dichloromethane at −78 °C (−108 °F) for 10 minutes. Trimethylsilyl triflate was added and reacts...
dehydrogenation. The ketone was converted into cyanohydrin 29 with trimethylsilylcyanide, potassium cyanide and a crown ether. As shown in Scheme 4, the bottom part...
Zinc cyanide is the inorganic compound with the formula Zn(CN)2. It is a white solid that is used mainly for electroplating zinc but also has more specialized...
linkages. One compound similar to diethylaluminium cyanide is bis[di(trimethylsilyl)methyl]aluminium cyanide, ((Me3Si)2CH)2AlCN, which has been shown crystallographically...
of the copper — alkene pi complex 2. On subsequent addition of trimethylsilylcyanide the Cu(III) species 3 is formed (indefinitely stable at that temperature)...
Sulfide 3 is first silylated by reaction with tert-butyllithium and then trimethylsilyl chloride 4 and then the second acyl proton is removed and reacted with...
treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst: RR’C=O + HCN → RR’C(OH)CN...
1002/14356007.a16_441. ISBN 978-3527306732.. Tom Livinghouse (1981). "TrimethylsilylCyanide: Cyanosilylation of p-Benzoquinone". Org. Synth. 60: 126. doi:10...
reaction of 1-Benzyl-4-phenyl-4-piperidinol [63843-83-4] (1) with trimethylsilylcyanide and subsequent Ritter reaction gave N-(1-Benzyl-4-phenylpiperidin-4-yl)formamide...
of the salt is tetrahedral at the boron atom. The electron-withdrawing cyanide substituent draws electron density away from the negatively charged boron;...
In organic synthesis, cyanation is the attachment or substitution of a cyanide group on various substrates. Such transformations are high-value because...
perrhenate ion reacts with the cyanide to give trans-[ReO2(CN)4]3−. Treatment of tetrabutylammonium perrhenate with trimethylsilyl chloride produces the oxychloride...
HC#C-C#CH + 2 KCl + 2 H2O}}} The bis(trimethylsilyl)-protected derivative may be prepared by the Hay coupling of (trimethylsilyl)acetylene: 2 Me 3 Si − C ≡ CH...
associated toxins. The alkali degradation products can be confirmed as their trimethylsilyl derivatives by gas chromatography/mass spectrometry.[citation needed]...
alcohol with net stereo-retention. MoOPH has also been shown to oxidize N-trimethylsilyl amides directly to the hydroxamic acid. Edwin Vedejs (April 15, 2001)...
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