2- Phenyl acrylic acid

Dupont et al. were able to obtain up to 80 % ee in the conversion of 2-phenyl-acrylic acid into (S)-2-phenylpropionic acid with the chiral [RuCl2(S)-BINAP]2NEt3 complex as catalyst in [BMIM][Bp4] melts (Scheme 5.2-9) [54]. 

Preliminary results from a study of catalytic activation of the heterocoupling between arylhalides and alkenes using pony-tail-functionalized dendrimer-encapsulated Pd nanoparticles have shown promise. For example, the classic Pd-catalyzed Heck coupling between arylhalides and methacrylate yields predominately (> 97%) the trans-cinnimaldehyde product [176]. On the other hand, the C02-soluble dendrimer nanocomposite exclusively catalyzes the production of the highly unfavored 2-phenyl-acrylic acid methyl ester isomer at 5000 psi and 75 °C (Fig. 27] [177]. 

BINAP core-functionalized dendrimers were synthesized by Fan et al. (36), via condensation of Frechet s polybenzyl ether dendritic wedges to 5,5 -diamino-BINAP (26—28). The various generations of BINAP core-functionalized dendrimers were tested in the ruthenium-catalyzed asymmetric hydrogenation of 2-[p-(2-methyl-propyl)phenyl]acrylic acid in the presence of 80 bar H2 pressure and in a 1 1 (v/v) methanol/toluene mixture. As later generations of the in situ prepared cymeneruthe-nium chloride dendritic catalysts were used, higher activities were observed (TOF values were 6.5, 8.3, and 214 h respectively). Relative to those of the BINAP... 

Nitro-phenyl)-acrylic acid ethyl ester... 

Related ligands for catalysis, namely BINAP ligands substituted with Frechet dendrons (5, Fig. 6.34) were prepared by Chan et al. [51]. They form rutheniu-m(II) complexes in situ, whose activity in the stereoselective hydrogenation of 2-[p-(2-methylpropyl)phenyl]acrylic acid was investigated. 

Willson TM, Henke BR, Momtahen TM, Charifson PS, Batchelor KW, Lubahn DB, Moore LB, Oliver BB, Sauls FIR, Triantafillou JA, Wolfe SG, Baer PG (1994) 3-[4-(l,2-Diphenylbut-l-enyl)phenyl]acrylic acid a non-steroidal estrogen with functional selectivity for bone over uterus in rats. J Med Chem 37 1550-1552... 

Preparation of cis/trans methyl-l-amino-2-cyclohexylethyl-l-methyl-(3-phenyl acrylic acid)phosphinate (generic procedure)... 

E)-3-Cyclopentyl-2-[3-fluoro-4-(5-methyl-tetrazol-l-yl)-phenyl]-acrylic acid methyl ester... 

Atropic acid a-phenyl acrylic acid C6H5C( CH2) CO2H 148,15... 

Cinnamic Aldehyde.—The other aromatic aldehyde which we shall mention is cinnamic aldehyde. It contains the aldehyde group in the side chain and not in the benzene ring, and is thus an aliphatic aldehyde substitution product of benzene. The aliphatic side chain is also an unsaturated chain. Its formula is CeHs—CH=CH—CHO, and it may be considered as beta-phenyl acrylic aldehyde. As an aldehyde it yields by oxidation an acid, viz., beta-phenyl acrylic acid or, as it is commonly known, cinnamic acid. The aldehyde is found in oil of cinnamon obtained from cinnamon bark, hence its name and the name of the acid. The most important synthesis is by the condensation of benzaldehyde and acetaldehyde, as follows ... 

Phenyl acetic acid. Hydro cinnamic acid. Cinnamic acid or Phenyl acrylic acid Phenyl propiolic acid. Phenyl vinyl acetic acid. 

Now hydrocinnamic acid bears exactly the same relationship to cinnamic acid, the former being phenyl propionic acid, the latter phenyl acrylic acid. 

Cinnamic acid beta-Phenyl acrylic acid... 

Atropic Acid.—A structural isomer of cinnamic acid is an acid obtained by loss of water from tropic acid and, therefore, known as atropic acid. It has been shown to be the alpha isomer of cinnamic acid, i.e,j alpha-phenyl acrylic acid, CeHs—C = CH2. Tropic acid is a... 

Recently, four generations of chiral diphosphine BI NAP-centered dendrimers were synthesized by Fan and coworkers via the condensation of Frechet-type dendrons with fR)-5,5 -diamino-BINAP (Figure 4.3) [32, 33]. The first- to third-generation BINAP dendrimers were tested in the Ru-catalyzed asymmetric hydrogenation of 2-[p-(2-methylpropyl)phenyl]-acrylic acid in methanol toluene (1 1, v/v) at room temperature (Scheme 4.2) [32]. The size of the dendrihc wedges was... 

Very recently, Fan et al. [13] reported on the use of a water-soluble PEO-substitut-ed first- and second-generation Frechet-type dendrimer with a chiral BINOL (1,1 -bi-2-naphthol) unit in catalysis. The enantiomeric excess in asymmetric hydrogenation of 2-[p-(2-methylpropyl)phenyl]acrylic acid with [RuCl(BINAP)(cymene)]Cl in an aqueous system was reported to increase upon addition of the dendritic... 

Hunsdiecker Reactions. The Hunsdiecker reaction is the de-carboxylative halogenation of metal carhoxylate salts. The reaction of a,/3-unsaturated carboxylic acids with NCS and catalytic lithium acetate in acetonitrile-water provides the corresponding /3-halostyrenes in moderate yields under mild conditions. The reaction proceeds with a good degree of stereospecificity. For example, the reaction of 3-(4-methoxy-phenyl)-acrylic acid with NCS with a catalytic amount of lithium acetate at room temperature provides l-(2-chloro-vinyl)-4-methoxybenzene in good yield (eq 23). 3... 

C10H10O2 tra s-3-phenyl-acrylic acid methyl ester 103-26-4... 

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