Naphthalenes phthalaldehydes

Chloroform, Chloropicrin, 1,1-Dichloroethylene, Endrin, Hexachlorocyclopentadiene, Methyl chloride. Methylene chloride, Tetrachloroethylene, 1,1,1 -Trichloroethane, Trichloroethylene Phosphine, see Pentachlorobenzene, Phorate Phosphoric acid, see Dichlorvos, Ethephon. Glvphosate. Malathion, Mevinphos, Parathion, Sulfotepp, Tributyl phosphate, Trichlorfon Phosphoric acid, dimethyl ester, see Mevinphos, Oxvdemeton-methvl Phosphorothioic acid, see Parathion Photoaldrin, see Aldrin Photoaldrin chlorohydrin, see Dieldrin Photodieldrin, see Aldrin, Dieldrin Photoheptachlor, see Heptachlor Photoketoaldrin, see Aldrin Phthalaldehyde, see Naphthalene Phthalaldehydes, see Tolnene Phthalic acid, see Anthracene, Benzo[a]anthracene, Benzyl bntyl phthalate, Dichlone. Diethyl phthalate, Dimethyl phthalate, Naphthalene, Naptalam. I ene... 

In a similar manner, phthalazine or its alkyl- or aryl-substituted derivatives are obtainable from 1,2-diacylarenes (Scheme 76). Phthalaldehydic acid and its analogs are transformed by hydrazines into the corresponding phthalazin-l(2//)-ones. Phthalazin-l(2iT)-one itself is prepared from naphthalene by oxidation, subsequent treatment with hydrazine and decarboxylation as shown in Scheme 77 (55YZ1423,64FRP1335759). 4-Substituted phthalazin-l(2iT)-ones are prepared in a similar way from 2-acylbenzoic acids. 3-Hydroxyphthalides,... 

Base-catalyzed condensation of 2-iminoindane-2-carbonitrile (62) with phthalaldehyde affords indeno[2,l-c]-2-benzazepine-5-carbonitrile (63) in excellent yield (95%),97 which is identical to an uncharacterizcd byproduct obtained earlier98 by condensing benzene-1,2-diacetonitrile with phthalaldehyde in the presence of sodium methoxide. The naphthalene analog 64 is prepared by condensing naphthalene-2,3-dicarbaldehyde with the indanecarbonitrile 62 under similar conditions. 

The initial discoveries of the extension of the aromatic ring of the ortho-phthalaldehyde (OPA) to a naphthalene-2,3-dicarboxaldehyde (NBA) and the substitution of cyanide (CN ) for 2-ME as the nucleophile have provided the Center with a much more versatile reagent system (5,11), which maintains the sensitivity for primary aliphatic amines and amino acids, and now is known to form fluorescent products with oligopeptides, proteins, and other related analytes that possess a primary amine function (Equation 1). 

The gas-phase reaction of N2O5 and naphthalene in an environmental chamber at room temperature resulted in the formation of 1- and 2-nitronaphthalene with approximate yields of 18 and 7.5%, respectively (Pitts et ah, 1985). The reaction of naphthalene with NOx to form nitronaphthalene was reported to occur in urban air from St. Louis, MO (Randahl et ah, 1982). The gas-phase reaction of naphthalene with OH radicals yielded phthalaldehyde, phthalic anhydride, phthalide, 1,4-naphthoquione, cis- and rra/J5-2-formylcinnamaldehyde, and 2,3-epoxy-1,4-naphthoquinone. 

Since BAs occurring in food do not exhibit satisfactory absorbance or fluorescence in the visible or ultraviolet range, chemical derivatization, either pre- (35-37) or postcolumn (38), is usually used for their detection in HPLC. The most frequently employed reagents for precolumn derivatization are fluorescamine, aminoquinolyl-lV-hydroxysuccinimidyl carbamate (AQC) (39, 40), 9-fluorenylmethyl chloroformate (FMOC) (41-43), 4-dimethylaminoazobenzene-4 -sul-fonyl chloride (dabsylchloride, DBS) (44), N-acetylcysteine (NAC) (45,46), and 5-dimethyl-amino-1-naphthalene-1-sulfonyl chloride (dansylchloride, DNS) (47,48), phthalaldehyde (PA), and orf/to-phthaldialdehyde (OPA) (49-51), together with thiols such as 3-mercaptopropionic acid (MPA) (37) and 2-mercaptoethanol (ME) (35,49). 

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. 

When naphthalene is degraded by permanganate under precisely defined conditions, phthalonic acid can be isolated instead of the usual phthalic acid, and this intermediate can be decarboxylated to phthalaldehydic acid (see page 1007) 150... 

K. Gyimesi-Forras, A. Leitner, K. Akasaka and W. Lindner, Comparative study on the use of ortho-phthalaldehyde, naphthalene-2,3-dicarboal-dehyde and anthracene-2,3-dicarboaldehyde reagents for a-amino acids followed by the enantiomer separation of the formed isoindolin-l-one derivatives using quinine-type chiral stationary phases,/. Chromatogr., A, 2005, 1083, 80-88. 

One of Clar s most notable early successes of the decade was pentacene 33. dar and John isolated 33 via dehydrogenation of a dihydropentacene isomer, several of which had been laboriously produced since 1911 when Phillipi first claimed one as 33 [28]. The combination of two groups efforts provided a far simpler route to pentacene two decades later. The highly efficient route began with condensation of o-phthalaldehyde and cydohexane-l,4-dione to afford quinone 34 (Scheme 1.10) [29]. Reduction with A1 powder afforded 33 in two steps [30]. Clar and coworkers also synthesized several pentacene derivatives in the 1940s 1.2-benzopentacene from pseduocumene and three additional dibenzopentacene derivatives from naphthalene and/or phenanthrene starting materials [la]. The syntheses focused on condensation cydization reactions of keto-adds to form the penultimate quinones and ultimate polycydes. 

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