140-29-4Relevant articles and documents
Microwave-assisted dehydration and chlorination using phosphonium salt
Tanji, Ken-Ichi,Koshio, Jiro,Sugimoto, Osamu
, p. 1983 - 1987 (2005)
Microwave-assisted reaction using phosphonium salt for dehydration of primary amides and chlorination of hydroxyheteroaromatics was carried out. Copyright Taylor & Francis, Inc.
A convenient preparation of alkyl nitriles by the Mitsunobu procedure
Wilk
, p. 2481 - 2484 (1993)
A convenient preparation of alkyl nitriles from alcohols extending the use of the Mitsunobu reaction is described. Acetone cyanohydrin is the acidic component and the source of cyanide ion.
Construction of enantioenriched polysubstituted hexahydropyridazines via a sequential multicatalytic process merging palladium catalysis and aminocatalysis
Marques,Giardinetti,Marrot,Coeffard,Moreau,Greck
, p. 2828 - 2832 (2016)
An efficient multicatalytic strategy for the construction of nitrogen-containing heterocycles has been reported. The powerful combination of organic and metal catalysis in a single vessel allowed the formation of enantioenriched polysubstituted cyclic 6-membered hydrazines bearing a quaternary stereocenter in good yields and selectivities.
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Shvartsberg et al.
, (1976)
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Nucleophilic Substitution Reaction of Alkyl Halide by Anion on a Macroporous Polymer Resin
Sukata, Kazuaki
, p. 4388 - 4390 (1985)
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Polycationic (Mixed) Core-Shell Dendrimers for Binding and Delivery of Inorganic/Organic Substrates
Kleij, Arjan W.,Coevering, Rob van de,Gebbink, Robertus J. M. Klein,Noordman, Anne-Marie,Spek, Anthony L.,Koten, Gerard van
, p. 181 - 192 (2001)
The convergent synthesis of a series of polycationic aryl ether dendrimers has been accomplished by a convenient procedure involving quantitative quaternarization of aryl(poly)amine core molecules. The series has been expanded to the preparation of the first polycationic, mixed core-shell dendrimer. All these dendrimers consist of an apolar core with a peripheral ionic layer which is surrounded by a less polar layer of dendritic wedges. These cationic, macromolecular species have been investigated for their ability to form assemblies with (anionic) guest molecules. The results obtained from UV/Vis and NMR spectroscopies, and MALDI-TOF-MS demonstrate that all the cationic sites throughout the dendrimer core are involved in ion pair formation with anionic guests giving predefined guest/host ratios up to 24. The large NMR spectroscopic shifts of resonances correlated with the groupings located in the core of the dendrimers, together with the relaxation time data indicate that the anionic guests are associated with the cationic core of these dendrimers. The X-ray molecular structure of the octacationic, tetra-arylsilane model derivative [Si(C6H3{CH2NMe3}2-3,5)4](8+) * 8I(-) shows that the iodide counterions are primarily located near the polycationic sphere. The new polycationic dendrimers have been investigated for their catalytic phase-transfer behavior and substrate delivery over a nanofiltration membrane.
Ionic liquids as catalytic green solvents for nucleophilic displacement reactions
Wheeler,West,Liotta,Eckert
, p. 887 - 888 (2001)
We demonstrate the use of room-temperature ionic liquids as a catalytic, environmentally benign solvent for the cyanide displacement on benzyl chloride, replacing phase-transfer catalyzed biphasic systems and thus eliminating the need for a volatile organic solvent and hazardous catalyst disposal.
The hydrogenation of mandelonitrile over a Pd/C catalyst: Towards a mechanistic understanding
McAllister, Mairi I.,Boulho, Cédric,McMillan, Liam,Gilpin, Lauren F.,Brennan, Colin,Lennon, David
, p. 26116 - 26125 (2019)
A carbon supported Pd catalyst is used in the liquid phase hydrogenation of the aromatic cyanohydrin mandelonitrile (C6H5CH(OH)CH2CN) to afford the primary amine phenethylamine (C6H5CH2CH2NH2). Employing a batch reactor, the desired primary amine is produced in 87% selectivity at reaction completion. Detection of the by-product 2-amino-1-phenylethanol (C6H5CH(OH)CH2NH2) accounts for the remaining 13% and closes the mass balance. The reaction mechanism is investigated, with a role for both hydrogenation and hydrogenolysis processes established.
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Vaughan,McCane
, p. 2504 (1954)
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HPLC-based kinetics assay facilitates analysis of systems with multiple reaction products and thermal enzyme denaturation
Klingaman, Chase A.,Wagner, Matthew J.,Brown, Justin R.,Klecker, John B.,Pauley, Ethan H.,Noldner, Colin J.,Mays, Jared R.
, p. 37 - 47 (2017)
Glucosinolates are plant secondary metabolites abundant in Brassica vegetables that are substrates for the enzyme myrosinase, a thioglucoside hydrolase. Enzyme-mediated hydrolysis of glucosinolates forms several organic products, including isothiocyanates (ITCs) that have been explored for their beneficial effects in humans. Myrosinase has been shown to be tolerant of non-natural glucosinolates, such as 2,2-diphenylethyl glucosinolate, and can facilitate their conversion to non-natural ITCs, some of which are leads for drug development. An HPLC-based method capable of analyzing this transformation for non-natural systems has been described. This current study describes (1) the Michaelis–Menten characterization of 2,2-diphenyethyl glucosinolate and (2) a parallel evaluation of this analogue and the natural analogue glucotropaeolin to evaluate effects of pH and temperature on rates of hydrolysis and product(s) formed. Methods described in this study provide the ability to simultaneously and independently analyze the kinetics of multiple reaction components. An unintended outcome of this work was the development of a modified Lambert W(x) which includes a parameter to account for the thermal denaturation of enzyme. The results of this study demonstrate that the action of Sinapis alba myrosinase on natural and non-natural glucosinolates is consistent under the explored range of experimental conditions and in relation to previous accounts.
Calixarene ionic liquids: Excellent phase transfer catalysts for nucleophilic substitution reaction in water
Yang, Fafu,Guo, Hongyu,Jiao, Ziyu,Li, Congcong,Ye, Jinqi
, p. 327 - 332 (2012)
The first examples of calixarene ionic liquids 3 and 6 with 3D-shaped cavities were obtained in high yields by reacting calix[4]arene or thiacalix[4]arene with 1,6-dibromohexane and then refluxing in 1-methylimidazole. The experiments of phase transfer catalysis in water suggested that they possessed excellent catalytic properties of aromatic nucleophilic substitution reaction and benzyl nucleophilic substitution. The optimized yields of product in catalytic reaction were as high as approximate 97% under mild reaction conditions. The cavities of calixarene skeleton played the crucial roles in catalysis and the stable cone conformation was favorable for catalysis.
Polymer-Supported Reagents: The Use of Polymer-Supported Cyanide and Thiocyanate to Prepare Nitriles, Thiocyanates, and Isothiocyanates
Harrison, Charles R.,Hodge, Philip
, p. 299 - 301 (1980)
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A poly(ethylene glycol)-supported quaternary ammonium salt: An efficient, recoverable, and recyclable phase-transfer catalyst
Annunziata, Rita,Benaglia, Maurizio,Cinquini, Mauro,Cozzi, Franco,Tocco, Graziella
, p. 1737 - 1739 (2000)
(matrix presented) A quaternary ammonium salt readily immobilized on a soluble poly(ethylene glycol) polymer support efficiently catalyzes different reactions carried out under phase-transfer catalysis conditions; the catalyst, easily recovered by precipitation and filtration, shows no appreciable loss of activity when recycled three times.
EFFECTS OF METAL IONS ON BENZYLGLUCOSINOLATE DEGRADATION IN LEPIDIUM SATIVUM SEED AUTOLYSATES
Hasapis, Xenophon,MacLeod, Alexander J.
, p. 559 - 564 (1982)
The effects of varying concentrations of Fe2+ (5E-5 - 5E-1 M) on benzylglucosinolate degradation in Lepidium sativum seed autolysates were investigated.Increased glucosinolate decomposition was observed over the whole range with a maximum effect at ca. 6E-3 M Fe2+, at which point glucosinolate degradation was more than three times that obtained in the absence of added Fe2+.Nitrile formation was especially enhanced in the presence of all concentrations of Fe2+ studied, and maximum amounts were obtained at ca. 6E-3 M Fe2+, when a more than four-fold increase over quantities produced in the absence of Fe2+ was observed.Thiocyanate formation was also promoted with a maximum at ca. 4E-3 M Fe2+, but isothiocyanate production was considerably reduced in all cases.It is suggested that Fe2+ inhibits isothiocyanate formation by interfering with the availability of ascorbic acid which is a proven co-factor for most thioglucosidase isoenzymes, but that an Fe2+-ascorbate complex might then be responsible for promoting enzymic production of nitrile.The effects of a limited range of concentrations of Fe3+ and Cu+ were also studied, and results related to those for Fe2+ The relevance of the findings to natural systems and to glucosinolate-containing foods is briefly discussed.Key Word Index-Lepidium sativum; Cruciferae; glucosinolate degradation.
Radical trifunctionalization of hexenenitrile via remote cyano migration
Chang, Chenyang,Wu, Xinxin,Zhang, Huihui,Zhu, Chen
supporting information, p. 1005 - 1008 (2022/02/01)
A novel radical-mediated trifunctionalization of hexenenitriles via the strategy of remote functional group migration is disclosed. A portfolio of functionalized hexenenitriles are employed as substrates. After difunctionalization of the unactivated alken
Iodine Promoted Conversion of Esters to Nitriles and Ketones under Metal-Free Conditions
Xiao, Jing,Guo, Fengzhe,Li, Yinfeng,Li, Fangshao,Li, Qiang,Tang, Zi-Long
, p. 2028 - 2035 (2021/02/03)
We report a novel strategy to prepare valuable nitriles and ketones through the conversion of esters under metal-free conditions. By using the I2/PCl3 system, various substrates including aliphatic and aromatic esters could react with acetonitrile and arenes to afford the desired products in good to excellent yields. This method is compatible with a number of functional groups and provides a simple and practical approach for the synthesis of nitrile compounds and aryl ketones.