5-Alkoxy-2-phenyl

In a search for liquid crystalline phases, a series of (/>-alkoxy-phenyl)isocyanide complexes was prepared from (Me2S)AuCl and the corresponding ligands RNG, where R = C H2n + iO-C6H4 with n = 2-12 (in even numbers).206 The chlorides were converted into the bromides and iodides in metathesis reactions using KBr/KI. Mesogenic behavior was found for most of the new materials with transition temperatures in the range from ca. 95 to 160 °C. 

There are dozens of linkers available for synthesis, and nearly all of them, once acylated by a protected amino acid, provide a benzyl ester or a benzyl amide that has been sensitized to cleavage by acid by the presence of electron-donating moieties such as alkoxy, phenyl, or substituted phenyl. There are cases in which a peptide chain is bound to a support through two different linkers in series. This allows for versatility in synthesis. The distinction between designation of a moiety affixed to a support as a handle or linker is sometimes arbitrary. 

No loss of optical purity was observed in the mild acidic hydrolysis of the enantiomerically pure 6-alkoxy -phenyl-5,6-dihydro-4/7-l,3-oxazine 132, which resulted in formation of (R)-3-benzoylamino-3-phenylpropanal 133 in excellent yield (Scheme 20). Hydrolysis of the analogous tetrahydro-l,3-oxazin-2-one 134 to 133 required a stronger acidic medium and took place only in poor yield, but without any decrease in the optical purity <20000L585, 2003JOC4338, 2004TL9589>. 

Hardy, Gy., Cser, F., Nyitrai, K., Samay, G. and Kallo, A. Investigation of the mesomorphic structure of p-alkoxy-phenyl-p-acryloyloxybenzoate polymers. J. Cryst. Growth, 48, 191 (1980)... 

The photocyclization of o-alkoxy phenyl ketones to yield benzofuranols (57 and 58) represents one of the earliest example of 8-H-abstraction from the lowest n, n triplet Wagner et al. [18] have provided detailed photokinetic data studying the photocyclization of a variety of o-alkoxyphenyl ketones 56, and have revealed that quantum efficiency for cyclization for 56d was the lowest (0.023) and that for 56f the highest (1.00). The diastereoselectivity for cyclization of 56 was found to be higher in benzene and lower in polar solvents. From the estimated kH values (0.6-25 x 106 s 1), it was inferred that the low rate constant for 56e (8 x 106 s ) compared to that for 56g (25 x 106s 1) i s due to the alkyl chain in the alkoxy groups that points away from the o-carbonyl moiety in the most populated equilibrium conformations (Table 8.1). 

B.-S. (1990) The photocyclization of o-alkoxy phenyl ketones. Journal of the American Chemical Society, 112, 5199-5211. 

Alkoxy-methyl-trifluor- E2, 858 Alkoxy-phenyl-trifluor- E2, 858 Alkoxy-tetraphenyl- E2, 887 Alkyl-tctrachlor- E2, 857 Alkyltriazenyliden-triamino- E2, 826 Allylamino-difluor-difluormethyl-hydro- E2, 836 Allyl-tetrachlor- XII/1, 343 Amino-bis-[2,2 -biphenyldiylJ- E2, 883 Amino-difluor-hydro-organo- E2, 836 Amino-organo-trifluor- E2, 859, 860 Aryl-(l-hydroxy-alkyl)-trifluor- E2, 864 Aryl-tetrachlor- E2, 857 Aryltriazenyliden-triamino- E2, 826 Benzyl-bis-[2,2 -biphenyldiyl]-... 

Aryl-tribrom- IX, 1132 Aryl-trichlor- IX, 1130 f. Bis-[3-nitro-alkoxy-phenyl]-dihydroxy- IX, 1025... 

Cationic poiymerization. In cationic chain polymerization the propagating species is a carbocation. Cationic polymerizations require monomers that have electron-releasing groups such as an alkoxy, phenyl, or a vinyl group (Table 14.20). 

C-Arylglycosides possess a stable C-C glycosidic linkage and exhibit a broad range of useful antitumor, antifungal and antibiotic properties. S.R. Pulley et al. developed a novel method for the synthesis of this important class of compounds by using the Dotz benzannuiation reaction between alkynyl glycosides and alkoxy phenyl chromium... 

On reflux in dimethylformamide solution, the dichlorocarbene adducts 4,6 and 8 of chromenes rearrange to give 3-(or 4-)chloro-l-benzoxepines 5, 7 and 9, respectively, in good yields, provided that the cyclopropane ring carries electron-donating substituents such as alkyl, alkoxy, phenyl, 4-methoxyphenyl or a 7c-excessive heterocycle such as 2-thienyl. 

Two-dimensional ion conduction was also achieved for the smectic liquid crystals consisting of the mixture of ionic liquids and hydroxyl-functionalized rod molecules [49-51] and smectic LC imidazolium salts having a long alkyl chain [52-55]. One-dimensional ion conduction was performed for aligned columnar LC phases forming ion-channels of fan-shaped imidazolium salts having a tris(alkoxy)phenyl moiety [56]. 

Scientists from GlaxoSmithKline (GSK) have examined several a-amino- and a-alkoxyphenyl propionic acid derivatives. They have also reported that a-alkoxy phenyl propionic acids are dual PPARa and PPARy agonists, whereas a-amino derivatives are a more selective PPARa agonist. Several oxadiazole-substituted a-isopropoxyphenylpro-pionic acids were evaluated. GSK scientists also made several L-tyrosine-based analogs. The compound selected (farglitazar, 50) was discontinued after phase III clinical trials, due to safety concerns (Scheme 19.15). 

Fig. 3.25. Chemical structure of a 2-fluoro-4-chloro-5-alkoxy phenyl imidazolidine triketone Protox inhibitor.

Subsequent research showed the SrnI mechanism to occur with many other aromatic compounds. The reaction was found to be initiated by solvated electrons, by electrochemical reduction, and by photoinitiated electron transferNot only I, but also Br, Cl, F, SCeHs, N(CH3)3, and 0P0(0CH2CH3)2 have been foimd to serve as electrofuges. In addition to amide ion, phosphanions, thiolate ions, benzeneselenolate ion (C HsSe"), ketone and ester enolate ions, as well as the conjugate bases of some other carbon acids, have been identified as nucleophiles. The SrnI reaction was observed with naphthalene, phenanthrene, and other polynuclear aromatic systems, and the presence of alkyl, alkoxy, phenyl, carboxylate, and benzoyl groups on the aromatic ring does not interfere with the reaction. ... 

Enantioselective additions of metal aryl species to ketones are more challenging transformations than the use of aldehydes as acceptors. This situation is related not only to the decreased reactivity of ketones as acceptors, but also to the greater difficulty for a Lewis acid to differentiate between the two lone pairs of a ketone carbonyl. An early example of an enantioselective phenyl transfer to aryl-alkyl ketones 23 was reported by Fu in 1998 (Scheme 8.7) [21]. The use of Noyori s dimethylaminoisobomeol (DAIB) Ugand 24 provided tertiary alcohols 25 in moderate to high yields and enantioselectivities. The addition of methanol was found to be necessary in order to form a mixed alkoxy phenyl zinc species which is less reactive than Ph2Zn. 

The thermodynamic data for the third series, the p-alkoxy-phenyl esters of terephthallc acid, are shown In Table 3. 

Columnar hexagonal phases of imidazolium and tris(alkoxy)phenyl moieties 3 and 4 containing polymerizable acrylate groups were synthesized by Kato etal. The columnar assembly was retained after photo-cross-linking. The obtained transparent polymer film was found to mediate anisotropic ion transport. The observed ion conduction is dependent on the orientation of columns, which indicates that the properties of these polymers are determined by the nanostructure of the resultant polymer, which in turn depends on both the structure of the surfactant monomer and the conditions adopted for the cross-linking reaction (Figure 3). 

Yoshio et al. have successfully designed and prepared ID anisotropically ion-conductive polymeric films by photopolymerization of aligned columnar liquid crystals of a fanshaped imidazohum salt [29], and these compounds have imidazohum and tris(alkoxy) phenyl moieties containing acrylate polymerizable groups at their periphery. The EJ2s and mixtures have many potential apphcations, such as used as an anisotropic medium for electrochemistry and apphed in dye-sensitized solar cells. 

FIGURE 14.11 Least restricted rotation around the C-C(=0) bond results in a cone curved by the alkoxy-phenyl groups in 59D[4],... 

Synthesis of 4-Alkoxy-phenyl-4-alkoxybenzoates Smectic C Materials. . . 429... 

Esters provide a wide range of stable smectic materials which are suitable for physical studies. In many instances they are more useful for investigations than Schiff s bases (nOms and TBnAs) because of their better stability and purity. Simple 4-alkoxy-phenyl 4-alkoxybenzoates are an intere.sting class of materials because they provide low temperature smectic C variants (often with the addition of smectic A and nematic phases). 

Alkoxy-substituted benzoyl-PEIs having Cs-Cij alkyl groups formed self-assembly of hexagonal, columnar, 2D phase.Molecular stmctures of self-assembling from poly (2-(3,4-bis(n-alkoxy)phenyl)-2-oxazoline)s were systematically investigated with regard to the DP and alkoxy chain... 

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