Phthalic dicarboxaldehyde

An interesting extrapolation of this synthesis deals with the preparation of the bispyridinium salt 62 from 1,2-phthalic dicarboxaldehyde and its subsequent reaction with primary amines (92BSB509).Tlie expected diimines 63 readily cyclize so that 2-aryl-l-arylimino-2,3-dihydro-l//-isoindoles 64 can be isolated in excellent yields (90-95%). Contrary to the reactions performed by employing the dialdehyde and amines directly, the syntheses involving the azinium salts do not produce those typical dark-colored complex mixtures of products (77JOC4217 85JHC449) (Scheme 20). 

The seminal work on deep-UV resist materials which incorporate chemical amplification was started at IBM San Jose s Research Laboratory in 1979 when FrSchet and Willson first prepared poly(4-t-butyloxycarbonyloxy styrene) and end-capped copolymers of o-phthalaldehyde and 3-nitro-l,2-phthalic dicarboxaldehyde. 

Kaale, E., Leonard, S., Van Schepdael, A., Roets, E., and Hoogmartens, J. (2000). Capillary electrophoresis analysis of gentamicin sulphate with UV detection after pre-capillary derivatization with 1,2-phthalic dicarboxaldehyde and mercaptoacetic acid. /. Chromatogr. A 895, 67—79. 

Coupling of alkynes with 1,.2-aryl dialdehydesThe complexes of Nb-CI3 DME (1) with alkynes react with phthalic dicarboxaldehyde to give, after workup with aqueous KOH, 2,3-disubstituted naphthols. In the case of unsymmetrical... 

When aldehydes, with or without a hydrogen, are treated with aluminum ethox-ide, one molecule is oxidized and another reduced, as in 19-81, but here they are found as the ester. The process is called the Tishchenko reaction. Crossed-Tishchenko reactions are also possible. With more strongly basic alkoxides, such as magnesium or sodium alkoxides, aldehydes with an a hydrogen give the aldol reaction. Treatment of a dialdehyde, such as phthalic dicarboxaldehyde (phthalaldehyde) with CaO, leads to a lactone.Like 19-81, this reaction has a mechanism that... 

An isoquinoline ring disconnection, with considerable potential, could not be brought to practical fruition until a 1,2-monoazabisylide was synthesised it involves Wittig and aza-Wittig condensations on phthalic dicarboxaldehyde to generate isoquinoline. 

Kanamycin Drug substance Sodium tetraborate, pH 10.0,16.0% methanol Derivatization with 1,2-phthalic dicarboxaldehyde/mercaptoacelic acid LOQ 0.14%... 

Three compounds also have two carboxyl groups the dicarboxylic acids. 1,2-Benzenedioc acid (phthalic acid, 35) has two carboxyl groups with an ortho relationship. In 1,3-benzenedioc acid (isophthalic acid), the carboxyl groups are meta, and in 1,4-benzenedioc acid (terephthalic acid) the carboxyl groups have a para relationship The dialdehyde compounds have related names 1,2-ben-zenedial (phthalaldehyde 36 also phthalic dicarboxaldehyde), 1,3-benzenedial (isophthalaldehyde also isophthalic dicarboxaldehyde), and 1,4-benzenedial (terephthalaldehyde also terephthalic dicarboxaldehyde). 

Ozonation of pentaphene (11) (shown below) in methylene chloride at —78°C. with one mole equivalent of ozone led to a peroxidic mixture which on oxidative workup led to 2,2 -binaphthyl-3,3 -dicarboxaldehyde (16) (16%), 2,2 -binaphthyl-3,3 -dicarboxylic acid (17) (16%), and phthalic acid (13) (2%) reductive workup (sodium iodide in acetic acid) gave 16 (25% ). In both cases, 28% of unreacted 11 was recovered. Ozonation of 11 with 4 mole equivalents of ozone followed by oxidative workup gave 2,2, 4,4, 5,5 -hexacarboxybiphenyl (18) (53%) and phthalic acid (13 ) (9% ). 

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