500899-63-8Relevant articles and documents
ALPHA-HYDROXY-BETA-AZIDO-TETRAZOLES
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Paragraph 0249; 0250, (2017/09/25)
Alpha-hydroxy-beta-azido tetrazole compounds of formula (I): a process for manufacturing alpha-hydroxy-beta-azido tetrazoles of formula (I), and their use for synthesizing new compounds, e.g. in “click” chemistry.
Expedient synthesis of glycidonitriles by darzens condensation of α-halogenonitriles with aldehydes and ketones
Jonczyk,Gadaj
, p. 1595 - 1610 (2008/09/17)
Chloroacetonitrile (1), α-halogenopropionitriles 4, and α-chlorophenylacetonitrile (6) react with aldehydes 2a,b,h-o and ketones 2c-g,p-t in the presence of solid NaOH in THF or DME, without any added catalyst, affording substituted glycidonitriles 3a-t, 5a, c-g,r,s and 7a,b,i,j,u,v, respectively (Darzens condensation). The glycidonitriles 3a-h, prepared from 1 and carbonyl compounds 2a-h, are obtained in high yields, exceeding those reported in the literature (Table 5). Expedient results of the reactions studied are due to increased reactivity of anions with Na+ as counterion in ethereal solvents. Investigation of the concentration of NaOH and the carbanion of diphenylacetonitrile in selected solvents reveals that ethereal solvents may increase the solubility of the anions participating in Darzens condensation.
Quaternary ammonium salts used as phase transfer catalyst
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, (2008/06/13)
Novel quaternary ammonium salts of general formula (I) STR1 wherein: R is a saturated or unsaturated, linear or branched alkyl radical of C1 to C8. R' is a saturated or unsaturated, linear or branched alkyl radical of C1 to C12, or a benzyl radical. n is a number equal to 2 or 3. Xθ is a halogenide anion, such as Clθ, Brθ, Iθ, are used as phase transfer catalysts, in heterogeneous ionic reactions wherein the reagents are in different phase and have different polarity.
NEW SYNTHETIC ROUTES TO β-FLUORO β-PHENYLLACTIC ACID DERIVATIVES AND Β-FLUOROCYANOHYDRINS
Ayi, A. I.,Remli, M.,Condom, R.,Guedj, R.
, p. 565 - 580 (2007/10/02)
Alkyl phenyl 2,3-epoxycarboxylates from the well-known Darzens glycidic esters synthesis react under very mild conditions with pyridinium-poly-hydrogen fluoride to give corresponding 3-fluoro 3-phenyllactates in almost quantitative yields with a high regio and stereoselectivity.This method can be applied succesfully to other flycidic derivatives: glycidoamides, glycidonitriles, glycidoiminoesters...The spectrometric properties (IR, NMR) are presented.
NOUVELLE VOIE DE SYNTHESE D'ACIDES AMINES MONOFLUORES
Ayi, A. I.,Remli, M.,Guedj, R.
, p. 1505 - 1508 (2007/10/02)
Ring opening of the glycidonitriles (IIa-e) by HF/pyridine leads to the fluorocyanohydrins (IIIa-e).Treatment of the nitriles (IIIa-e) with ammonia in methanol gives the α-amino-β-fluoro nitriles (IVa-e) which upon acidic hydrolysis afford the β-fluoro-α-
Two-phase Darzens Condensation Reaction with Octopus Compounds as a Catalyst
Akabori, Sadatoshi,Ohtomi, Michiko,Yatabe, Seiichi
, p. 1463 - 1464 (2007/10/02)
The octopus compound, readily derived from hexakis(mercaptomethyl)benzene and 1-chloro-3,6,9-triozadecane, was effectively employed as a catalyst in the two-phase Darzens condensation of carbonyl compounds with chloroacetonitrile to afford the correspondi