Naphthalene-2,3-dialdehyde

Amines are another important group of analytes. Mellbin and Smith [72] compared three different fluorescent reagents, dansyl chloride, 4-chloro-7-nitrobenzo-1,2,5-oxadiazole, and o-phthaldialdehyde, for derivatization of alkylamines. The dansyl tag was found to be the most effective. Hamachi et al. [73] described the application of an HPLC-POCL method for determination of a fluorescent derivative of the synthetic peptide ebiratide. Another comparative study was done by Kwakman et al. [74], where naphthalene-2,3-dialdehyde and anthracene-2,3-dial-dehyde were evaluated as precolumn labeling agents for primary amines. The anthracene-2,3-dialdehyde derivatives were not stable, especially in the presence of hydrogen peroxide, and the POCL detection of these derivatives was therefore... 

Blood and urine Separation in a Conway microdiffusion cell treatment of absorber solution with naphthalene-2,3-dialdehyde and taurine Spectrophotofluoro- metric 0.8 ppb 66-82.6 at 0.0013-0.13 ppm (blood) 75.6-82 at 0.0013-0.13 ppm (urine) Sano et al. 1989... 

Sano A, Takezawa M, Takitani S. 1989. Spectrofluorometric determination of cyanide in blood and urine with naphthalene-2,3-dialdehyde and taurine. Anal Chim Acta 225 351-358. 

Primary amines Naphthalene-2,3-dialdehyde Anthracene-2,3-di aldehyde 74... 

A few examples of formation of two carbon-carbon bonds were also reported. 2,7-Di-/>-chlorobenzoylnaphtho[2 3 -4 5]thiepine 19 was prepared by condensation of di-/>-chlorophenacyl sulfide 211 with naphthalene-2,3-dialdehyde 210 in 2 1 dioxane-MeOH containing a catalytic amount of NaOH in 80% yield (Equation 31) <2004MI326>. The compound 19 exhibited the property as a flexible host molecule (Section 13.03.3.1). 

Sample preparation Condition a 100 mg C18 SPE cartridge (Varian) with 1 mL MeCN water 75 25 and 1 mL 10 mM HCl in MeCNiwater 5 95. Mix 100 [xL plasma with 25 pL 1 M citric acid and 100 pL 1 pg/mL IS in 50 mM sodium dihydrogen phosphate, add to the SPE cartridge, wash with 1 mL 10 mM HCl in MeCN water 5 95, elute with 400 pL MeCN water 75 25, add 50 pL 20 mM KCN in 200 mM pH 6.5 phosphate buffer to the eluate, add 50 pL 20 mM naphthalene-2,3-dialdehyde in MeCN, vortex, heat at 40° for 45 min. Evaporate to dryness under reduced pressure at room temperature, reconstitute the residue with 100 pL 50 mM sodium dihydrogen phosphate, centrifuge, inject a 40 pL aliquot. 

Finally, we have also attempted to improve on the fluorescence and chemiluminescence efficiencies of the labeling reagent, the naphthalene dialdehyde. Derivatives 7, 8, and 9 (Table IX) have been synthesized and studied. As shown in Table IX, none of these new derivatives presents an advantage over the parent unsubstituted CBI-Ala. 

Photolytic. Based on data for structurally similar compounds, acenaphthylene may undergo photolysis to yield quinones (U.S. EPA, 1985). In a toluene solution, irradiation of acenaphthylene at various temperatures and concentrations all resulted in the formation of dimers. In water, ozonation products included 1,8-naphthalene dialdehyde, 1,8-naphthalene anhydride, 1,2-epoxyacenaphthylene, and 1-naphthoic acid. In methanol, ozonation products included 1,8-naphthalene dialdehyde, 1,8-naphthalene anhydride, methyl 8-formyl-1-naphthoate, and dimethoxyacetal 1,8-naphthalene dialdehyde (Chen et al., 1979). Acenaphthylene reacts with photochemically produced OH radicals and ozone in the atmosphere. The rate constants and corresponding half-life for the vapor-phase reaction of acenaphthylene with OH radicals (500,000/cm ) at 25 °C are 8.44 x lO " cmVmolecule-sec and 5 h, respectively. The rate constants and corresponding half-life for the vapor-phase reaction of acenaphthylene with ozone at 25 °C are... 

Chemical/Physical. Ozonation in water at 60 °C produced 1,8-naphthalene dialdehyde, 1,8-naphthalene anhydride, 1,2-epoxyacenaphthylene, 1-naphthoic acid, and 1,8-naphthaldehydic acid (Calvert and Pitts, 1966). 

Naphthalene dialdehyde, see Acenaphthylene Naphthalene-l,8-dicarboxylic acid, see Acenaphthene Naphthalene-2,3-dicarboxylic acid/anhydride, see... 

Formylation HF-SbFs catalyzes formylation of polynuclear aromatic compounds with carbon monoxide. Thus naphthalene affords 1,5-naphthalene-dialdehyde in 53% yield. 

A stream of nitrogen containing O3 passed into a soln. of acenaphthylene in methanol at —30° during 0.5 hr., the reaction stopped just before the yellow color of the startg. m. completely disappears, the cooling bath removed, glacial acetic acid and KI added, stirred 1 hr. while the mixture warms to room temp., then 10%-Na-thiosulfate soln. added until the iodine color is discharged 1,8-naphthalene dialdehyde hydrate. Y 73.5% only 16.5% with a J. K. Stille and R. T. Foster, J. Org. Chem. 28, 2703 (1963). 

A different behavior is exhibited by naphthalene-1,8-dicarbocal-dehyde (73). No m-naphthane derivatives are obtained on reaction with nitromethane, nitroethane or other methylene components. The basic medium, required for aldol type additions, causes the dialdehyde to undergo Cannizzaro reaction to the naphthopyranon (74) via an intramolecular 1,5-hydride shift, which is sterically favoured by the peri-position of the two aldehyde functions 28). 

Stille and Foster studied the ozonization of acenaphthylene (1) to naphthalene-1,8-dialdehyde hydrate (2) and found that with ozone in a stream of nitrogen a yield of 73.5% can be realized, whereas with the usual oxygen-ozone mixture the yield was only 16.5%. 

In the case of aromatic dialdehydes, the cyclization is frequently accompanied by dehydration Thus, o-phthalaldehyde cyclizes when treated with nitromethane in the presence of alcoholic potassium hydroxide (Scheme 6) to give the flci-nitro salt that undergoes dehydration by acidification with mineral acid to form 2-nitroinden-l-ol (35). This reaction was discovered in 1910 by Thiele and Weitz and can be considered the first demonstrated example of the cyclization of a dialdehyde with nitromethane. Like o-phthalaldehyde, naphthalene-2,3-dicarbaldehyde and o-benzoylbenzaldehyde undergo ready cyclization with nitromethane under similar reaction conditions to form respectively, 2-nitrobenzinden-l-ol (equation 7) and two isomeric o-nitrohydroxyindenes (36) and (37) (equation 8) upon acidification with mineral acid. The cyclization with nitromethane also works well with suitable diketones such as bicy-clo[3.3.1]nonane-3,7-diones where the carbonyl groups are favorably oriented for cyclization on treatment with nitromethane and sodium methoxide the corresponding 2-nitroadamantane-l,3-diols (equation 9) are obtained in fair to good yields. 

Some aromatic compounds can also react with ozone, although most simple aromatic rings such as benzene derivatives and naphthalene do not. Anthracene reacts with ozone to give anthraquinone in 73% yield after an oxidative workup. Indeed, quinone formation is a more typical example of the reaction of ozone with aromatic compounds (for other oxidative cleavage reactions see sec. 3.8 and for oxidation to phenols and quinones see sec. 3.3). Only a reactive n bond, such as the 9,10 bond of phenanthrene, will oxidatively cleave, and phenanthrene (361) was oxidized to dialdehyde 362 upon treatment with ozone in methanol followed by a workup with potassium iodide in acetic acid. ... 

The analogues (24) of tropic acid have been made from the pentose dialdehyde derivative using the Grlgnard reagent derived from naphthalene acetic acld.- ... 

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