1,8-Naphthalic anhydride, reaction with

Naphthalic anhydride, reaction with potassium hydroxide to yield 2,6-naphthalenedicarboxylic add, 40, 71... 

Naphthalic anhydride, reaction with potassium hydroxide to yield 2,6-naphthalenedicarboxylic add, 71 N-a-Naphthylpiperidine, 7S N- Naphthylpiperidine, 74 Neopentyl alcohol, 76 t-Nitrobenzenesulfonyl chloride, reduction to f -nitrophenyl disulfide by hydriodic acid, 80... 

On reaction with zinc dust in alkaline medium, naphthalic acid is subjected to reductive dimerization with so-called deoxynaphthalic anhydride 366 as the result (13CB1484). The formation of diarylnaphthalides 371 on... 

There are known methods for constructing a naphtho[ ]-l, 2-diazepine nucleus by ring expansion on interaction of naphtho[crf]pyran derivatives with hydrazines. Thus, the reaction of naphthalic anhydride with hydrazines leads to 3,10-dioxo derivatives of naptho[[Pg.88]

The naphthalimide ring system has the drawback of low effectiveness, which is mainly attributable to the low molar extinction coefficient. The industrial synthesis of alkoxynaphthalimides begins with acenaphthene. Chlorination and subsequent oxidation with dichromate give the corresponding naphthalic acids [116], which are converted to the anhydrides on drying. Mild reaction with methyla-mine, followed by reaction with sodium methoxide or sodium ethoxide, gives, e.g., 64 or 65. 

Fig. 13.144 (1) sulfonation, (2) chromate oxidation to give the naphthalic anhydride (64), (3) condensation with A-methylamine, and (4) replacement of the sulfonic acid group in a reaction with methoxide. This process gives C.I. Fluorescent Brightener 162. 

J. W. Cook introduced the method of cyclizing an o-aroylbenzoic acid to an anthraquinone by heating the keto acid with phosphorus pentoxide in nitrobenzene at 150-165 . For example, the isomeric acids (3) and (4) resulting from the Friedel-Crafts reaction of 1,2-naphthalic anhydride with thiophene are cyclized to the same quinone (5). ... 

Novel bis(naphthalic anhydrides) containing bridging groupings and/or bulky substituents are reviewed. Reactions of these compounds with aromatic diamines and bis(o-phenylene diamines) led to the formation of polynaphthylimides and polynaphthoylenebenzimidazoles combining solubility in organic solvents with high thermal, heat and chemical resistance. 

Similar reactions were also employed for preparation of sulfide- and sulfone-containing bis(naphthalic anhydrides). Thus, the interaction of 4-bromo-naphthalic anhydride with sodium sulfide yields 4,4 -sulfide-bis(naphthalic anhydride) [92, 93] ... 

Thus, the interaction of dioxo- and dithio-bis(naphthalic anhydrides) with 4,4 -diaminodiphenyl oxide, as shown in Scheme 39 [97, 98] resulted in poly-naphthylimides with ether and thioether groups, which were soluble in phenolic solvents. Reactions were carried out in m-cresol at 10% concentration using quinoline or iso-quinoline as catalyst. 

Polynaphthylimide with iV-naphthylimide orfho-sutetituents was prepared by the reaction of 3,3 -diamino-4,4 -di(p-aminophenoxy) diphenyl sulfone [164] with an equimolar amount of bis(naphthalic anhydride) followed by treatment with a two-fold molar amount of naphthalic anhydride in a m-cr ol-benzoic acid medium under the conditions of high-temperature catalytic polycondensation. The polymer was soluble in phenolic, amide solvents as well as in tetrachloroethane its molecular mass was of the order of 60 000, the softening temperature 340 °C and the temperature of 10 % mass loss 480 °C (Table 16). 

Anhydrides of dithioic acids have a dithioate moiety. Thiothionophthalic anhydride 198 was prepared with a 85% yield by treating dithioacetal 199 with LDA in THE containing 0.83 equiv of HMPA (Scheme 42) [123]. The compound 198 loses a sulfur atom over 110 °C, dimerizing to 200, like the unsubstituted thiothionophthalic anhydride [124]. An improved synthesis of and some reactions of trithio-l,8-naphthalic anhydride (201) has been reported (Eq. 38) [125]. 

The reaction is completed within 5-15 min if tetralin at 210 °C is used as solvent. Also, dithio-y-lactones, including dithio-phthalides and dithio-Q -p)Tones, are formed smoothly whereas the hitherto unknown simple or 3-dithiolactones cannot be prepared, neither with LR nor by any other method. Interestingly, dithiopilocarpine is formed as a mixture of diastereomers on reaction of pilocarpine with LR (eq 16), i.e. both oxygen atoms of (12) are replaced by sulfur. In an interesting sequence of thion-ation and rearrangement reactions, three different thiono analogs of 1,8-naphthalic anhydride were prepared (eq 17). ... 

These data reveal a logical pathway to a possible enhancement in thermal and chemical stability of polyheteroarylenes, Le. in the above mentioned reactions a replacement of bis(phthalic anhydrides) by bi naphthalic) ones the structure of which would determine the formation of systems containing six-membered imide rings - either isolated ones or those condensed with other heterocyclic moieties. 

The process to manufacture the perylene chromophore is basically unchanged since its discovery in the early 1900s. The reaction sequence begins with catalyzed air oxidation of a coal tar extract, acenaphthene (2), to produce naphthalic acid anhydride (3). There are several catalysts, such as V2OS, that are used Commercially in this oxidation reaction. Naphthahc acid anhydride is available from several global suppliers in a range of purities. 

Picoline reacts with phthalic anhydride in the presence of zinc chloride or acetic anhydride to give pyrophthalone . Much work has been done on the structure of this compound . Perhaps the best formulationl is (30). Similar reactions occur with naphthalic and diphenic anhydride and in the cases of lutidines and collidines are assumed to occur at the 2-methyl group. Under similar conditions 2-picoline gives (31) with benzene-sulphonylbenzisothiazolone . 

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