Anthracene-1,8-dialdehyde

The 8 Hz coupling indicates a proton in the y-position (B) the 5 Hz coupling locates a vicinal proton in position a (C), the additional 0.9 Hz coupling locates the remaining proton in position a (D) and thereby the p-position of the substituent. 

The substruetures A - D aeeount for eleven of the total of twelve double bond equivalents so that the eompound eontains one additional ring as present in anthraeene or phenanthrene skeletons. 

From all symmetrically substituted anthracene and phenanthrene dialdehydes E - H containing 1,2,3-trisubstituted benzene rings, 

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

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... 

Horner-Wadsworth-Emmons procedures are also commonplace in synthetic materials chemistry, recent examples including donor-acceptor substituted molecules with bicyclo-spacers, which require napthalene-, anthracene-, and pyrene-substituted phosphonates, (112), (113) and (114) respectively, well-defined, electroactive PPE/PPV copolymers through the condensation of dialdehydes and bisphosphonate (115), ° and triphenylamine-substituted PPV. ° ... 

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. ... 

By HPLC the major reaction products of the BaP-D system were separated and tentative chemical structures were assigned to the peaks, based on the interpretation of the low and high resolution nS data as well as on comparison with reference spectra. The reaction mixture consisted mainly of ring-opened compounds such as dialdehyde and dicarboxylic acid, but also contained disubstitution products such as diphenols and quinones. The benzo(de)anthracene-7-one 3,4-dicarboxylic acid found in the reaction mixture is probably the precursor to the benzo(de)anthracene-7-one, detected by Sawicki (48) in the extract of ambient aerosols. The benzo(a)pyrene quinones were discovered in ambient air by Pierce and Katz (34). 

Synthesis of Arene Oxides. Reaction of (Me2N)3P with aromatic dialdehydes provides arene oxides such as benz[a]anthracene 5,6-oxide (2a) (eq 5). These compounds, also known as oxiranes, are relatively reactive, undergoing thermal and acid-catalyzed rearrangement to phenols and facile hydrolysis to dihydrodiols. Consequently, their preparation and purification requires mild reagents and condition.s. The importance of this is underlined by successful synthesis of the reactive arene oxide (2b) in 75% yield using appropriate care, despite a previous report of failure of the method. While compound (2b) is a relatively potent mutagen, it is rapidly detoxified by mammalian cells. The principal limitation of the method is the unavailability of the dialdehyde precursors, which are obtained through oxidation of the parent hydrocarbons, e.g. by ozonolysis. 

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