Propionitrile phenyl

The formation of ethyl cyano(pentafluorophenyl)acetate illustrates the intermolecular nucleophilic displacement of fluoride ion from an aromatic ring by a stabilized carbanion. The reaction proceeds readily as a result of the activation imparted by the electron-withdrawing fluorine atoms. The selective hydrolysis of a cyano ester to a nitrile has been described. (Pentafluorophenyl)acetonitrile has also been prepared by cyanide displacement on (pentafluorophenyl)methyl halides. However, this direct displacement is always aecompanied by an undesirable side reaetion to yield 15-20% of 2,3-bis(pentafluoro-phenyl)propionitrile. 

Phenyl-propionitrile, CgHj. CH.2. CH2. CN, is present in nssturtium oil. It is a powerfully smelling oil, boiling at 261°. On hydrolysis by alcoholic potash it yields phenyl-propionic acid, melting at 47°. 

Propanenitrile, 2-(4-nitrophenyl>2-phenyl-[Propionitrile, 2-(4-mtrophenyl)-2-phenyl-], 55, 94... 

Chloro-3-(/>-nitrophenyl)propionitrile 247 / -Nitroaniline (4.2 kg) is dissolved in a hot mixture of concentrated HC1 (91) and water (91), cooled to 30°, and treated with ice (24 kg). 30% Sodium nitrite solution (7.3 1) is run in within a few minutes with vigorous cooling. The diazonium salt solution is filtered and treated with a solution of acrylonitrile (1.76 kg) in acetone (15 1). CuCl2 (600 g) is then added and a short time thereafter at ca. 18° evolution of nitrogen begins. The temperature is kept below 30° by ice-cooling. 2-Chloro-3-(p-nitro-phenyl)propionitrile separates and after recrystallization from methanol has m.p. 110° (yield 5.3 kg). 

While propylene gives primarily 73, styrene gives exclusively the phenyl-substituted derivative corresponding to 74. It is noteworthy in this connection that hydrocyanation of propylene (using a Ni[P(Ootolyl)3]3 catalyst) gives primarily n-butyronitrile, while styrene gives predominantly the branched product 2-phenyl-propionitrile. ... 

Oxy i [3-nitiro-ph6nyl] a-[4-nitro phenyl]-propionitril 10 II227. 

A mixture of p-nitrobenzaldehyde and trimethylsilylacetonitrile treated with a small amount of a soln. of K-tetramethoxoaluminate in pyridine, and refluxed 9 hrs. at an oil bath temp, of 160-180° under anhydrous conditions in a Ng-atmosphere y -trimethylsiloxy- -(p-nitrophenyl)propionitrile (Y 78%) refluxed 1 hr. in alcohol containing a little coned. HGl -> -hydroxy-y -(p-nitro-phenyl)propionitrile (Y 83%). F. e. s. L. Birkofer, A. Ritter, and H. Wieden, B.95, 971 (1962). 

It is unfortunate that the data concerning the relative contributions of enthalpy and entropy terms to solvent reorganization around the transition state for proton-transfer is not only scanty but contradictory. The rate of proton-transfer from (-l-)-2-methyl-3-phenyl propionitrile to methoxide, as followed by the optical activity change [43], is accelerated by a factor of 10 in per cent DMSO as compared with pure methanol solvent. This increase in rate is due entirely to a decrease in AH from 30.9 to 24.4 k cal mol The value of also decreases, from 10.6 to 6.0cal mol , so tending to... 

The decarboxylation of 2-cyano-2-phenylpropionic acid 20, a model compound of 14 was also investigated by the same authors [14]. While cinchonine 8 provided (S)-2-phenyl propionitrile 21 in only 13% ee, 9-ept-cinchona-benzamides 19b and 18b confirmed their superiority over the parent cinchona alkaloids affording 21 with up to 61% ee (Scheme 3.7). 

Furthermore, Agrobacterium tumefaciens d3, which was enriched on racemic 2-phen-ylpropionitrile as the sole source of nitrogen, was used for the conversion of 2-arylpro-pionitriles to the corresponding (5)-acids [63]. The conversion of both racemic 2-phenyl-propionitrile and -amide by whole cells led to the formation of the (S)-acid with an e.e. above 96% after 47.5% conversion and was caused by the combined action of an (5)-specific nitrile hydratase and a highly (5)-specific amidase (Fig, 17). The stereoselectivity of the nitrile hydratase was used for the preparation of (5)-amides by whole cells in the presence of an amidase inhibitor or with the purified nitrile hydratase [64]. The highest... 

---