2-phenylacrylonitrile

Reactivities of Side-chains of Monocyclic Thiophens.—The protonation of various furan- and thiophen-carboxamides in aqueous sulphur acid solution has been investigated by u.v. spectroscopy. The values of pKbh that were calculated using the acidity function and the Bunnett-Olsen linear free-energy relationship indicate the lower basicity of furan- and thiophen-2-carboxamides with respect to that of benzamides and of the 3-derivatives. The kinetics of isomerization of cw-l-(2-thienyl)-2-phenylacrylonitrile, as well as of its 2-furyl and 2-selenienyl analogues, have been studied in a solution of decahydronaph-thalene, with methanesulphonic acid and potassium t-butoxide as catalysts, and the mechanism has been discussed. ... 

The final product of this reaction is 2-amino-4-phenylpyrimidine. I5N-Labeling showed that the net substitution takes place by the ANRORC mechanism rather than by an AE process. The related sequence is shown in Scheme 2. Isolation of 3-amino-3-phenylacrylonitrile (39) in low yields at -75°C suggests that a parallel pathway via adduct 37 is also possible. However, the latter has not been detected in the reaction mixture. 

Using 3-phenylacrylonitrile, the same procedure affords 6,6r-diphenyl-4,4 -bis(1,2,3-dithiazin-4-yl) (2) in 75% yield.4... 

POLYMETHACRYLONITRILE, POLY-a-PHENYLACRYLONITRILE, POLY-a-CHLOROACRYLONITRILE AND POLYVINYLIDENE CYANIDE [141]... 

The behaviour of pure poly-a-phenylacrylonitrile is similar to that of polymethacrylonitrile. A strong exotherm which suggests a rapid cycliz-ation is nevertheless observed in the presence of 9% KCN as additive. 

The two adducts (254) and (255) are formed from the irradiation of trans-stilbene in the presence of rra 5-3-phenylacrylonitrile. The two adducts are themselves photolabile and are converted into cis- and /ram-stilbene and cis- and... 

Triazine 2-imines 18d-g are available from 4,6-disubstituted-l,2,3-triazines with 0-(mesitylenesulfonyl)hy-droxylamine (MSH) followed by treatment with potassium carbonate solution (Equation 19) <1988YZ1056>. N-2 Amination failed for monosubstituted 1,2,3-triazines 86a and 86b using both MSH and hydroxylamine-O-sulfonic acid (HOS). In the latter two cases, ring degradation by base occurred and only the 3-amino-2(3)-phenylacrylonitriles 98a and 98b were isolated as products, presumably via action of base on the intermediates 97. Lack of a substituent at C-6 of 86a and 86b was regarded as responsible for this failure <2004EJO4234> (Equation 20). 

Acrylonitrile has been reduced in DMF containing tetraalkylammonium iodides in dilute solutions of the substrate conversion to propionitrile occurs but at higher concentrations dimerisation to adiponitrile pre-vails. /5-phenylacrylonitrile forms the hydrodimer, 2,3-diphenyl adiponitrile. ... 

Although examples are few, stereospecific HR of 1,2-disubstituted alkenes such as cinnamate under controlled conditions is known [7,26]. As another example, ( )-3,3-diarylacrylonitrile 101 was obtained selectively by the reaction of ( )-3-phenylacrylonitrile with p-iodoanisole [61]. HR of methyl o-hydroxycinnamate with p-iodotoluene afforded the coumarin 102, showing that the tolyl and ester groups are trans as expected [62]. 

CAS 4360-47-8 EINECS/ELINCS 224-441-5 Synonyms Ceylanyle Cinnamalva Cinnamyl nitrile p-Phenylacrylonitrile 3-Phenyl-2-propenenitrile 2-Propenenitrile, 3-phenyl-Classification Aromatic nitrile Definition Commercial prod, is an isomer mixt. with typ. b.p. 253-254 C Empirical C9H7N... 

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... 

P-Phenylacrylonitrile. See Cinnamonitrile (E)-3-Phenylacrylonitrile trans-3-Phenylacrylontrile trans-P-Phenylacrylontrile. See trans-Cinnamonitrile P-Phenylacryloyl chloride trans-3-Phenylacryloyl propenoyl chloride Phenylacrylyl chloride. See Cinnamoyl chloride... 

MBH acetates undergo smooth nucleophilic substitution with sodium azide in water under mild conditions to afford the corresponding ethyl 2-azido-methyl-3-phenylpropenoates 299 and 2-azidomethyl-3-phenylacrylonitriles 300 in excellent yields (Scheme 3.128). °... 

Catalytic reduction of the o-(o-nitroaryl)acrylonitriles (Xl-84) over a palladium catalyst at room temperature gave the amine (XI-8S). Reduction with iron in boiling acetic acid yielded the indole XI-83, however. In an earlier work by Walker, catalytic (palladium, 80°) reduction of the corresponding -phenylacrylonitriles (XI-86) caused reductive cyclization of the nitrile to give the indole XI-87. An attempt was made to apply Walker s method to the 2-pyridyl isomer of XI-84 but the expected indole was not isolated. The mechanism proposed for the cyclization of XI-84 to the indole (XI-83 Py = 2-Pyridyl) involves an intramolecular Michael addition of a hydroxylamino group to the double bond rather than attack by an amino group. Support for... 

Reaction mixture heated at 100 °C for 6 h to afford ( -2-formyl-3-phenylacrylonitrile (162) (42.0 mg, 49 % formed as an inseparable 3.5 1 mixture with trani-cinnamaldehyde) as a pale yellow oil. 

Bis(trimethysilyl)methane derivatives react with aldehydes and ketones in the presence of a fluoride ion to afford di- and trisubstituted alkenes in one pot [56]. The reaction involves the fluoride-catalyzed carbonyl addition followed by Peterson elimination. For example, a,a-bis(trimethylsilyl)acetonitrile 153 produces /3-phenylacrylonitrile 154 with high -selectivity, whereas tris(trimethylsilyl)-methane 155 reacts with anisaldehyde at room temperature to give alkenylsilane 156 (Scheme 5.39). 

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