Azomethines. II. Courbes d'absorption et constitution de bisazométhines

The intense [M -17]+ ion, which is a characteristic feature of the mass spectra of N-a-nitrobenzylideneaniline and its simple derivatives, may be substantially reduced in intensity when the aniline-derived ring is also ortho substituted: the intensity is lowest when this ortho substituent has a nucleophilic character and can itself interact with the CH=N group. The ortho substituents examined are Br, CH,, OH, NHa, SH, SC6H4CH3@), C0,CH3 and COICIH5.

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o‐Nitrobenzylidene compounds. I—Competitive ortho interactions in the mass spectra of n‐o‐nitrobenzylidene‐o‐substituted anilines

Johnston

Smart

Smith

1976

Org. Mass Spectrom.

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Synthesis of conjugated Schiff‐base polymers

Hodgkin

Heller

1970

J. polym. sci., C Polym. symp.

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SYNOPSISAttempts to synthesize conjugated polymers with cyanine dyes attached to the conjugated backbone are described. The experimental approach is to prepare and characterize conjugated polymers with attached quinolinium ions and then to convert these to dyes by reaction with lepidinium methiodide. Aromatic Schiff-base polymers were chosen as the conjugated backbone. Since unsubstituted Schiff bases show very little conjugation, a series of model compounds and model polymers were prepared and their electronic spectra were determined in order to correlate the effect of substituents on electron delocalization.Efforts are being made to prepare high molecular weight polymers by a Schiff-base exchange reaction. The syntheses of various monomers for the Schiff-base exchange reaction are described.

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Carbonyl and thiocarbonyl compounds XX. Reaction of hydroxybenzaldehydes with o‐phenylenediamine; newer aspects in benzimidazole synthesis

Latif

Mishriky

Assad

1983

Recl. Trav. Chim. Pays‐Bas

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The nature of the products of the uncatalysed reaction of the o‐hydroxybenzaldehydes 1a‐d with o‐phenylenediamine in boiling ethanol is mainly dependent on the molar ratio of the reactants and the nature of the substituents at the phenyl ring of the aldehyde. In contrast, the m‐ and p‐hydroxy analogues 1e‐g afford exclusively the corresponding 1‐aralkyl‐2‐arylbenzimidazoles 6, regardless of these factors. However, at low temperature, the hydroxybenzaldehydes 1a‐g react with the diamine always giving monoanils (2) regardless of the hydroxy position. The monoanils of the o‐hydroxy aldehydes afford predominantly 2‐arylbenzimidazoles (4) when boiled in n‐butanol. In contrast, those of the m‐ and p‐hydroxy analogues give exclusively 1‐aralkyl‐2‐arylbenzimidazoles (6), whereas, when heated in nitrobenzene, 2‐arylbenzimidazoles (4) are readily obtained. The dianils 5a‐d, upon boiling in butanol, give a mixture of 2‐arylbenzimidazoles (4) and 1‐aralkyl‐2‐arylbenzimidazoles (6), the ratio of which is dependent on the nature of the substituents at the aldehyde. Reaction mechanisms and spectral features of the products are discussed.

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Azomethines. II. Courbes d'absorption et constitution de bisazométhines

Cited by 5 publications

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o‐Nitrobenzylidene compounds. I—Competitive ortho interactions in the mass spectra of n‐o‐nitrobenzylidene‐o‐substituted anilines

o‐Nitrobenzylidene compounds. I—Competitive ortho interactions in the mass spectra of n‐o‐nitrobenzylidene‐o‐substituted anilines

Synthesis of conjugated Schiff‐base polymers

Carbonyl and thiocarbonyl compounds XX. Reaction of hydroxybenzaldehydes with o‐phenylenediamine; newer aspects in benzimidazole synthesis

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