Conversion of Aldoximes into Nitriles with Raney Nickel in Refluxing 2-Propanol

Aldoximes are readily dehydrated to nitriles with Raney nickel in refluxing 2-propanol.     

First report of the direct supporting of palladium–arginine complex on boehmite nanoparticles and application in the synthesis of 5‐substituted tetrazoles

Boehmite nanoparticles are aluminium oxide hydroxide (γ‐AlOOH) particles, which were prepared using a simple and inexpensive procedure in water at room temperature and further modified using arginine. Subsequently palladium particles were immobilized on their surface to prepare Pd‐Arg@boehmite. This novel nanostructured compound was fully characterized using thermogravimetric analysis, X‐ray diffraction, inductively coupled plasma optical emission (ICP‐OES) and energy‐dispersive X‐ray spectroscopies, and scanning and transmission electron microscopies. Finally, this catalyst was applied as a moisture‐ and air‐stable heterogeneous material for the synthesis of 5‐substituted 1H –tetrazole derivatives. The leaching of palladium and heterogeneity of the catalyst were studied using hot filtration and ICP‐OES. This catalyst demonstrated remarkable recyclability. The novelty of this work is that it represents the first time an amino acid has been grafted on boehmite nanoparticles.     

New Preparation of (Z)-1-Phenyl-3-cyano-2-propen-1-ones

Reaction of γ-phenyl-β,γ-unsaturated hydroxamates with bis(collidine)bromine(I) hexafluorophosphate led to the formation of cyclic bromo imidates. Reaction of these with triethylamine led to the formation of 3-cyano-2-propen-1-ones with good yields by a fragmentation reaction.     

Nitrile Rubber Reactor Operation Troubleshooting with Principal Component Analysis

Principal Component Analysis (PCA) is employed as a tool in order to demonstrate yet another application of the technique, and, most importantly, to show that results from the statistical multivariate technique do make physico-chemical sense. The operation of a typical emulsion copolymerization of acrylonitrile and butadiene (nitrile butadiene rubber, NBR) is used as an example of process troubleshooting. In more general terms, a statistical tool is used to aid process data analysis and process operation (recipe, product property) troubleshooting.

The goal is to produce consistent Mooney Viscosity (MV) among different batches. The observation is that varying induction times lead to Mooney Viscosity inconsistencies. Firstly, we show results from the application of PCA to process data. Secondly, we deal with an even more important (and often ignored) question by examining whether the trends indicated by PCA make process sense.     

Nanoalloy Based on Clays: Intercalated‐Exfoliated Layered Silicate in High Performance Elastomer

A novel method is described for the preparation of nanocomposites comprising a high performance rubber for tire application and layered silicates clay. In this work nanocomposites of solution‐styrene butadiene rubber (S‐SBR) with montmorillonite layered silicate were prepared with carboxylated nitrile rubber (XNBR), a polar rubber, as a compatibilizer. A sufficient amount of organomodified layered silicate was loaded in carboxylated nitrile rubber (XNBR) and this compound was blended as a master batch in the S‐SBR. Mixed intercalated/exfoliated morphologies in the nanocomposite are evinced by X‐ray diffraction measurements and transmission electron microscopy. Dynamic mechanical analysis also supports the compatibility of the composites. A good dispersion of the layered silicate in the S‐SBR matrix was reflected from the physical properties of the nanocomposites, especially in terms of tensile strength and high elongation properties.     

Sequential 1,3-Dipolar Cycloadditions in the Synthesis of Novel Tri-spiro Cyclohexanones and Piperidin-4-ones

The sequential 1,3-dipolar cycloadditions of azomethine ylide and nitrile oxide to a series of 2,6-bis[(E)-arylmethylidene]cyclohexanones and 1-methyl-3,5-bis[(E)-arylmethylidene]tetrahydro-4(1H)-pyridinones afforded novel tri-spiro heterocycles comprising isoxazoline, pyrrolidine and acenaphthylen-1(2H)-one rings in good yields and stereoselectivity.     

Copper-Catalyzed Cyanopropylation of Activated Alkenes

A practical copper-catalyzed alkylarylation of activated alkenes with azobisisobutyronitrile (AIBN) and beyond has been developed, in which incorporation of 3^o nitrile moiety into an oxindole scaffold proceeded smoothly through cascade radical addition/C(sp²)-H cyclization. The use of readily available AIBN as radical source and inexpensive CuI as catalyst, as well as broad substrate scope and the simplicity of operation and handling, make this protocol a highly attractive approach to oxindoles bearing 3^o nitrile moiety.     

Highly Regioselective Conversion of Epoxides to β-Hydroxy Nitriles with Cyanide Exchange Resin

Abstract

A simple and regioselective method is described for the efficient conversion of epoxides to β-hydroxy nitriles using Amberlite IRA-400 supported cyanide. The reactions occur in the absence of catalyst and furnish the corresponding β-hydroxy nitriles in high yields.