Synthesis nitriles

Nitrile Synthesis. Cyanogen bromide [506-68-3] condenses with toluene in the presence of aluminum chloride to give -tolunittile (129). 

Both methods of nitrile synthesis—SN2 displacement by CN- on an alkyl halide and amide dehydration—are useful, but the synthesis from amides is more general because it is not limited by steric hindrance. 

NITRILE SYNTHESIS USING A NEW ENZYME, ALDOXIME DEHYDRATASE... 

Aldoximes are prepared from aldehydes and hydroxylamine by condensation reaction, and the dehydration reaction of aldoxime is one of the most important methods of nitrile synthesis in organic chemistry." We speculated that it would become one of the most important examples in Green Chemistry if the dehydration reaction could be realized by an enzymatic method, and started studies on a new enzyme, aldoxime dehydratase, and its use in enzymatic nitrile synthesis. Furthermore, we clarified the relationship between aldoxime dehydratase and nitrile-degrading enzymes in the genome of the microorganisms and the physiological role of the enzyme. 

Preparation of Nitriles Investigated in Micro Reactors Organic synthesis 4 [OS 4] Nitrile synthesis from a-bromotoluene... 

Catalytic asymmetric cyanide addition to imines constitutes an important C—C bondforming reaction, as the product amino nitriles may be converted to non-proteogenic a-amino acids. Kobayashi and co-workers have developed two different versions of the Zr-catalyzed amino nitrile synthesis [73]. The first variant is summarized in Scheme 6.22. The bimetallic complex 65, formed from two molecules of 6-Br-binol and one molecule of 2-Br-binol in the presence of two molecules of Zr(OtBu)4 and N-methylimidazole, was proposed as the active catalytic species. This hypothesis was based on various NMR studies more rigorous kinetic data are not as yet available. Nonetheless, as depicted in Scheme 6.22, reaction of o-hydroxyl imine 66 with 5 mol% 65 and 1—1.5 equiv. Bu3SnCN (CH2C12, —45 °C) leads to the formation of amino nitrile 67 with 91 % ee and in 92 % isolated yield. As is also shown in Scheme 6.22, electron-withdrawing (— 68) and electron-rich (—> 69), as well as more sterically hindered aryl substituents (— 70) readily undergo asymmetric cyanide addition. 

Chloropropionitrile, 50, 20 Chlorosulfonyl isocyanate, in nitrile synthesis, SO, 52 precautions, 50,18... 

DMF at room temperature. Solid-phase-mediated iso nitrile synthesis under microwave irradiation led to much faster reactions and in many cases improved yields therefore, allowing rapid access to this important class of compounds, amenable for a broad range of subsequent synthesis. 

Nickel-metal bonds, binuclear and polynuclear complexes, homometallic clusters, 8, 111 Nickel nanoparticles, preparation, 12, 87 Nickel-nitriles, synthesis and reactivity, 8, 150 Nickelocenes... 

The reaction of primary aliphatic halides and alkali metal cyanides - the Kolbe Nitrile Synthesis - gives nitriles in good yields. 

The Kolbe Nitrile Synthesis is a typical SN2 reaction, which runs best in polar aprotic solvents (DMSO, acetone) ... 

Miller, J. A. Dankwardt, J. W. Penney, J. M. Nickel-catalyzed cross-coupling and amination reactions of aryl nitriles. Synthesis 2003, 1643-1648. 

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