19690-00-7Relevant academic research and scientific papers
Selective silylation of alcohols, phenols and oximes using N-chlorosaccharin as an efficient catalyst under mild and solvent-free conditions
Aghapour, Ghasem,Moghaddam, Ali Kazemi,Nadali, Samaneh
, p. 197 - 203 (2015/05/12)
Efficient silylation of OH group in alcohols, phenols and oximes is described using a catalytic amount of N-chlorosaccharin and hexamethyldisilazane (HMDS) under mild and solvent-free conditions. This silylation reaction can be carried out with excellent and interesting various selectivities.
Sulfated zirconia: An efficient catalyst for solvent-free synthesis of silyl ethers under mild conditions
Thirupathi, Boningari,Prasad, Avvari N.,Srinivas, Rapelli,Reddy, Benjaram M.
experimental part, p. 2064 - 2072 (2011/07/30)
Oximes, allylic, aliphatic, aromatic, cyclic, acyclic, and hetero alcohols are silylated in short reaction times with good yields in the midst of a catalytic amount of sulfated zirconia solid acid catalyst and trimethylsilyl cyanide under nonbasic, solvent-free, and ambient temperature conditions. Selectivity toward O-silyl ether rather than N-silyl ether has been observed. This simple experimental procedure, combined with easy recovery and reusability of the catalyst, is expected to contribute to the development of a clean and environmentally friendly strategy for the synthesis of O-silyl ethers. Copyright
An Efficient Synthesis of Dinitrile Derivatives by the Reaction of Oxime Esters or Acid Anhydrides with Cyanotrimethylsilane Catalyzed by La(OiPr)3
Fujii, Akiko,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 6209 - 6212 (2007/10/03)
The reaction of oxime esters with cyanotrimethylsilane (Me3SiCN) under the influence of a catalytic amount of lanthanide compounds produced α-trimethylsilyloxydinitrile derivatives in excellent yields accompanied with the formation of trimethylsilyl oxime ethers. Among the lanthanoid catalysts examined, La(OiPr)3 was found to be the best catalyst. The reaction seems to proceed through the formation of acyl cyanides as intermediates, followed by the addition of Me3SiCN to them. Additionally, the reaction of acetic anhydride with Me3SiCN catalyzed by La(OiPr)3 gave 1-trimethylsilyloxyethane dinitrile. Thus, various α-trimethylsilyloxydinitriles were synthesized in good yields by allowing oxime esters or acid anhydrides to react with Me3SiCN in the presence of a catalytic amount of La(OiPr)3.
A New Synthesis of Oxime Derivatives from Carbonyl Compounds and N,O-Bis(trimethylsilyl)hydroxylamine
Hoffman, Robert V.,Buntain, Gregory A.
, p. 831 - 833 (2007/10/02)
Reaction of a series of aldehydes and ketones with the potassium salt of N,O-bis(trimethylsilyl)hydroxylamine (2) gave high yields of the corresponding oximate anion 5.This anion, formed in a Peterson-type reaction, could be protonated to the oxime 7 or trapped in situ with a variety of electrophiles to give O-substituted oxime derivatives.
O-trialkylstannyl oximes
Harrison,Zuckerman
, p. 175 - 181 (2007/10/12)
Fourth-group oximes have been synthesized from (a) the organoelement chlorides and the oxime in the presence of a strong Lewis base, (b) organotin chlorides with the O-lithio oxime to split out lithium chloride, and (c) bis(organotin) oxides and organotin hydroxides, ethoxides, and diethylamines with the oxime to split out water, ethanol, and diethylamine, respectively. The products are monomeric in solution; all are liquids except O-trimethylstannylcyclohexanone oxime whose ir spectrum differs from that in solution and whose mass spectrum shows peaks above the parent mass which are revealed by high-resolution work to contain the Sn-O-Sn backbone, presumably resulting from cyclic Sn-O-Sn-O structures in the solid. Confirmation of the high-coordination solid state structure comes from Sn119m M?ssbauer quadrupole splitting values which are ca. 1 mm/sec higher for the trimethyltin derivatives. The O-trialkyltin oximes undergo metathetical reactions with water and hydrogen chloride and with other fourth group chlorides to give the silicon and germanium analogs, and insertion reactions with isocyanates, isothiocyanates, chloral, bromal, etc., to give novel adducts where reactivity is seen to be in the orders Sn > Ge ? Si and SnOR > SnON=C 3CCHO > C6H5NCO > RNCO > C6H5NCS.
