Nitriles cinnamonitrile

Other substituted olefins such as acrylonitrile, fumaronitrile, crotono-nitrile, cinnamonitrile, and diethylfumarate also formed adducts with Co (DMG)2 complexes containing py, H2O, or PBuj and, in one case, with [Co (DMG-BF2)2py]. Second-order rate constants were reported for the formation of several Tr-olefin-Co(I) complexes from organocobalt(III) complexes containing, for example, NCCH2CH2- with DMG, DPG, DMG-BF, py, H2O, and PBuj. 

The method described is a modification of the procedure used by Ghosez to synthesize cinnamonitrile. 3-(2-Furyl)acrylo-nitrile has been prepared by catalytic condensation of furfural with acetonitrile in the vapor phase at 320°, by dehydration of the corresponding amide over phosphorus pentachloride, and by decarboxylation of 3-(2-furyl)-2-cyanoacrylic acid. ... 

Wagner and co-workers explored the different selectivity of 1,3-dipolar cyclo additions of nitrones 140 and cinnamonitrile 139 leading to oxadia-zolines 141 derived from an exclusive CN attack instead of a C = C attack (Scheme 50). This behavior was observed when cinnamonitrile was coordinated to a transition metal like Ft or Pd [89]. A similar approach to platimun-promoted nitrile-nitrone cyclo additions was reported using cychc nitrones. In this case, the authors reported a higher stereoselectivity of cychc nitrones with respect to the acyclic nitrones, due to a rigid E conformation adopted by cyclic nitrones [90]. 

It is interesting to note that reduction of cinnamonitrile, related to aromatic nitriles, gives dimers. Electrochemical dimerization of acrylonitrile is a well-known industrial process of the... 

Cinnamonitrile can be prepared by one of the common routes to nitriles, e.g., by dehydration of cinnamaldoxime. It is stable to alkali and is used for perfuming soap and detergents. 

Analogous ring closures are to be found in the cyclizations of cinnamonitriles (191 R1 = C1, R2 = H and R OH, R2 = Ar) to 2-benzazepin-l-ones (192) and (193 R = aryl) with hydrogen chloride and polyphosphoric acid respectively (74AHC(17)45>. Polyphosphoric acid has also been used to effect cyclization of the mono- or di-nitriles (191 R1 = OH,... 

It is interesting that reduction of cinnamonitrile, related aromatic nitriles, and acrylonitrile gives dimers, Scheme 3-4 ... 

SYNTHESIS OF a,g-UNSATlIRATED NITRILES FROM ACETONITRILE PREPARATION OF CYCLOHEXYLIOENEACETONITRILE AND CINNAMONITRILE (Acetonitrile, cyclohexyl1 dene- and 2-Propenen1trlle, 3-phenyl, (E)-)... 

This method is highly selective for unsaturated ketones and aldehydes, whereas reduction of a,p-un-saturated carboxylic acid derivatives, such as esters, amides and nitriles, is very sluggish. Thus, benz-ylideneacetone was selectively and cleanly reduced in the presence of methyl cinnamate, cinnamonitrile or cinnamamide. ... 

Cinnamonitrile (9) and substituted analogues are easier to reduce than the simple nitriles and form less reactive radical anions. The mechanism and kinetics of the EHD of 9 has therefore been much studied. In DMF n 1, and RRDE measurements were in agreement with the RR mechanism at substrate concentrations <8 mM [55]. The rate constant for the rate-determining dimerization step (RR mechanism) has been determined by several methods in DMF (Table 3). In liquid ammonia T = —43°C), dimerization is considerably slower (Table 3), and, significantly, even in the presence of /-PrOH the coulometric n-value was small (0.05-0.27), indicating considerable polymerization [52]. 

The other procedure10 illustrates a general method for conversion of carboxylic acids into the corresponding nitriles. Treatment of cinnamic acid (4) with chlorosulfonyl isocyanate gives the carboxylic acid amide N-sulfonyl chloride (5). As above, treatment of (5) with DMF gives cinnamonitrile (6) in 78-87% yield. 

A thesis of l,4-dihydrop3nidazines has been reported by reacting pyruvaldehyde-l-arylhydrazones 17 with a,jS-unsaturated nitriles 18. Thus, 17a reacts readily with a-substituted cinnamonitriles 18 through Michael addition at the CH site to yield dihydroamino pyridazines 20. NMR cannot however exclude a possible initial addition of the hydra-zone NH site to the activated double bond in 18 yielding 21 that then would cyclize to isomeric 6H-pyridazine derivatives 22. The structure of the products was shown to be 4H-pyridazines 20 by an X-ray crystal structure of compound 20c (2007JHC105, 2007JHC877 ... 

Only a small percent of styrene copolymers reported in the literature achieved industrial importance. Some of the interesting copolymers of styrene that were reported but not utilized commercially are copolymers with various unsaturated nitriles. This includes vinvlidine cyanide, fumaronitrile, malononitrile, methacrylonitrile, acrylonitrile, and cinnamonitrile. Often, copolymerization of styrene with nitriles yields copolymers with higher heat distortion temperature, higher tensiles, better craze resistance, and higher percent elongation. 

CAS 1885-38-7 EINECS/ELINCS 217-552-5 Synonyms (E)-Cinnamonitrile Cinnamonitrile, predominantly trans trans-Cinnamyl nitrile trans-p-Cyanostyrene (E)-3-Phenylacrylonitrile trans-3-Phenylacrylontrile trans-p-Phenylacrylontrile (E)-3-Phenylpropenenitrile (E)-3-Phenyl-2-propenenitrile trans-3-Phenylpropenonitrile... 

Cinnamyl nitrile. See Cinnamonitrile trans-Cinnamyl nitrile. Seetrans-Cinnamonitrile Cinnamyl phenylacetate CAS 7492-65-1 EINECS/ELINCS 231-322-1 FEMA 2300... 

Cedarwood oil Cinnamonitrile trans-Cinnamonitrile Cinnamyl anthranilate Citral Citral dimethyl acetal Citronella (Cymbopogon nardus) oil 3-Citronellol Citronellyl nitrile Citronellyloxy acetaldehyde Cyclamen homoaldehyde Cyclohexyl phenethyl ether trans-4-Decenal 9-Decenol 9-Decenyl acetate... 

Olefinic and benzenoid nitriles were obtained in high yields, for example, ben-zonitrile (88%), 4-riitrobenzonitrile (85%), cinnamonitrile (95%). Anti-fural-doxime gave a 60% yield of the nitrile. 

Pb-tetraacetate added portionwise with ice-cooling during 0.5 hr. to a soln. of frans-cinnamaldehyde in dry benzene through which a stream of NHg-gas is passed, and stirring continued 3 hrs. fran -cinnamonitrile. Y 89%.—This simple and convenient method can be used for the prepn. of a great variety of nitriles. F. e. s. K. N. Parameswaran and O. M. Friedman, Ghem. Ind. 1965, 988. 

Use of acrylo nitrile in place of acrylic acid in this method (Scheme 55) yield the corresponding cinnamonitriles. Most of the products obtained in Heck-reactions are almost exclusively (E) isomers. However, the reaction of acrylonitrile give a mixture of (E) and (Z) isomers with ratio 3 1, close to that observed under conventional anhydrous conditions. ... 

---