Adler oxidation

The two halogen-based methods that continue to attract organic chemists the most for the oxidative activation of arenois are the Adler oxidation and the Pelter oxidation (vide infra) ... 

JACOBSEN C, HARTVIGSEN K, THOMSEN M K, HANSEN L F, LUND P, SKIBSTED L H, H0LMER G, ADLER-NissEN J and MEYER A s (2001) Lipid oxidation in fish oil enriched mayonnaise calcimn disodium ethylenediaminetetraacetate, but not gallic acid, strongly inhibited oxidative deterioration, J Agric Food Chem, 49, 1009-19. 

Adler, K.B., Akiey, N.J. and Holdenstaufier, W.J. (1989). Exposure of airway epithelium to extracellular oxidants in vitro stimulates arachidonic acid metabolism and mucin secretion. Am. Rev. Resp. Dis. 139, A403. 

Igalson J, Adler JG (1983) Effect of hydrogen-isotope implantation on aluminum oxide tunnel-junction barriers. Phys Rev B 28 4970-4975... 

Factors Governing Oxygen Reduction in Solid Oxide Fuel Cell Cathodes Stuart B. Adler... 

When 2D or 3D PAHs are considered then the choice becomes much larger. An exhaustive review on the advances in the synthesis of polycyclic aromatic compounds can be found in Harvey, 2004. The most used strategies are flash vacuum pyrolysis, cross-coupling, oxidative photocyclization, Diels-Adler cycloaddition, etc. 

By means of Fremy salt oxidation, Adler and Lundquist (5) estimated that about half of the phenolic units contain free S-positions in M.W.L. Mikawa (J/), by Mannich reaction, obtained evidence that about 25-40% of the phenolic units in his sulfate lignin preparation contained no substituent in 5-position. In this investigation we also conclude that at least one-third of the phenolic units in our kraft lignin preparation has free 5-positions. 

Adler S.B., Wilson J.R., Schwartz D.T. (2003) Nonlinear harmonic response of mixed-conducting SOFC cathodes. In Solid Oxide Fuel Cells VIII (SOFC-VIII), Electrochemical Society Proceedings, 2003-07, S.C. Singhal and M. Dokiya (Eds.), The Electrochemical Society, Pennington, NJ, pp. 516-524. 

Fichter, F., Adler, M. (1927) Electrochemical oxidation of nuclear chlorinated hydrocarbons. Helv. Chim. Acta. 9, 287. 

Larger patterned surfaces can also be achieved using inkjet printing. This technique has been used to create micron-sized letters of the alphabet containing diphenylalanine peptide nanotubes [tertbutoxycarbonyl-Phe-Phe-OH (Boc-Phe-Phe-OH)] on either transparent foil or indium-tin oxide (Adler-Abramovich and Gazit, 2008) as shown in Figure 13. This later... 

McMillan K, Adler M, Auld DS, Baldwin JJ, Blasko E, Browne LJ, Chelsky D, Davey D, Dolle RE, Eagen KA, Erickson S, Feldman RI, Glaser CB, Mallari C, Morrissey MM, Ohlmeyer MHJ, Pan G, Parkinson JF, Phillips GB, Polokoff MA, Sigal NH, Vergona R, Whitlow M, Young TA, Devlin JJ, Allosteric inhibitors of inducible nitric oxide synthase dimerization discovered via combinatorial chemistry, Proc. Natl. Acad. Sci. USA, 97 1506-1511, 2000. 

Uncondensed phenolic units in lignin have been estimated by a color reaction based on oxidation with potassium nitrosodisulfonate (Fremy s salt) (Adler and Lundquist 1961) as illustrated below ... 

To eliminate interfering side reactions caused by units having carbonyl and hydroxyl groups at the a-position, the lignin is reduced with borohydride and alkylated with methanolic hydrochloric acid prior to oxidation to convert these groups to o-quinones. Following a procedure based on the above reaction, spruce milled-wood lignin was found to contain 15-18% of uncondensed phenolic units (Adler and Lundquist 1961). 

Another factor which may influence the yield of acids obtained from lignin in wood is the presence of easily hydrolyzable aryl ether linkages such as those represented by phenylpropane-a-aryl ether structures In phenolic units, such structures are easily cleaved even under very mild alkaline conditions (Adler et al 1968) Therefore, it can be assumed that, in the alkylation step of the oxidative degradation procedure, a partial hydrolysis of such structures may occur, thereby creating new phenolic end groups that may affect the analysis... 

A method developed by Adler et al. (1958) is based on the oxidation of simple phenolic guaiacyl (Adler and Hernestam 1955) or syringyl (Chang et al. 1975) compounds with aqueous sodium periodate solution to ortho-quinone structures in which process nearly lmol of methanol per mol of phenolic hydroxyl group is released [Eq. (1)]. 

The procedure described below, a modified version of the method developed by Adler et al. (1958) and Gierer et al. (1964), is applicable to both lignin and lignocellulosic samples. The general procedure consists of oxidation of the sample with an aqueous sodium periodate solution and a direct measurement of the liberated methanol in the presence of an internal standard. 

Although the periodate oxidation and aminolysis methods provide quantitative data on the frequency with which of phenolic hydroxyl groups occur in lignin, they do not reveal the structural environment in which they occur. Such information may be obtained by other means, e.g., UV spectroscopic or chemical degradation methods (Adler 1977). 

Adler E (1977) Lignin chemistry - past, present, and future Wood Sci Technol 11 169-218 Adler E, Hernestam S (1955) Estimation of phenolic hydroxyl groups in lignin I Periodate oxidation of guaiacol compounds Acta Chem Scand 9 319-334 Adler E, Hernestam S, Wallden I (1958) Estimation of phenolic hydroxyl groups in lignin Sven Papperstidn 61 64-647... 

Pahlman, A.K., Granath, K., Ansell, R., Hohmann, S., and Adler, L., 2001, The yeast glycerol 3-phosphatases Gpplp and Gpp2p are required for glycerol biosynthesis and differentially involved in the cellular responses to osmotic, anaerobic, and oxidative stress. J. Biol. Chem. 276(5) 3555-3563. 

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