982. Syntheses of substituted amino-, aminovinyl-, and aminobutadienyl-p-quinones

Buckley, Daniel J.; Henbest, H. B.; Slade, Peter

doi:10.1039/jr9570004891

Cited by 51 publications

(20 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The "coupled merocyanine model" is also appropriate for 3 and 4 which exhibit very similar spectral properties in comparison to 1 [21,22]. For 5, however, due to the stronger coupling of the pentamethine moieties via the central CC bond, the localizability indices are significantly lower (cf .…”

Section: A the Electronic States Of 25-diamino -Guinonementioning

confidence: 99%

“…Whereas in the case of the coupled merocyanine structure 2b the CT contributions play an important role in the description of the lowest excited state of 2, the local excitation of the H-chromophor predominates in respect to the In hexane [21]. 2,5-dichlor-3,6-bis-2-diethylaminovinyl-be~oquinone in dioxan [22]. 1,5-diarnino-naphthochinone(2,6) in dimethyl sulfoxide [23].…”

Section: B the Electronic States Of The Bispyrrol-indigomentioning

confidence: 99%

See 1 more Smart Citation

MO‐LCAO‐Calculations on polymethines. V. PPP‐type calculations and configuration analyses of simple prototype dyes in terms of molecular subsystems

Fabian

Tröger‐Naake

1977

Int J of Quantum Chemistry

View full text Add to dashboard Cite

AbstractsIn order to elucidate certain controversies in interpreting the a-electronic structure of some simple quinone and indigo dyes the Pariser-Parr-Pople sca,,-wave-functions have been subjected to configuration analyses. Whereas 2,5-diamino-quinone (1) can be excellently represented by coupling of two trimethine-merocyanine chains, the analogous consideration is less appropriate with bispyrrolindigo (2). In this case the results of the configuration analyses indicate clearly the limited applicability of the Longuet/Higgins-Murrell-method.Pour tlucider des controverses dans I'interprttation de la structure Clectronique a des simples colorants quinoidique et indigoi'dique les fonctions de type Pariser-Parr-Pople S C~.~ furent soumises a des analyses configurationelles. Tandis que le 2,5-diamino-quinone (1) peut btre reprtsentt excellemment par un couplage des deux chahes trimethine-merocyaninique une consideration analogue est moins correcte pour le bispyrrol-indigo (2). Dans ce cas les rtsultats des analyses configurationelles indiquent clairement l'applicabilitit limitte de la mtthode de Longuet-Higgins et Murrell.Um Widerspriiche bei der Interpretation der P-Elektronstruktur von einigen einfachen Chinon-und Indigofarbstoffen zu klken, wurden Pariser-Parr-Pople-scp,,-Wellenfunktionen Konfigurationsanalysen unterworfen. Wihrend 2,s-Diamino-chinon (1) sehr gut durch Kopplung zweier Trimethin-merocyaninketten wiedergegeben werden kann, ist die gleiche Betrachtungsweise fur Bispyrrol-indigo (2) weniger geeignet. In diesem Falle lassen die Ergebnisse der Konfigurationsanalyse deutlich die begrenzte Anwendungsbreite der Longuet/Higgins-Murrell-Methode erkennen.

show abstract

Section: A the Electronic States Of 25-diamino -Guinonementioning

confidence: 99%

Section: B the Electronic States Of The Bispyrrol-indigomentioning

confidence: 99%

MO‐LCAO‐Calculations on polymethines. V. PPP‐type calculations and configuration analyses of simple prototype dyes in terms of molecular subsystems

Fabian

Tröger‐Naake

1977

Int J of Quantum Chemistry

View full text Add to dashboard Cite

show abstract

“…Chloranil undergoes facile nucleophilic displacement reactions with primary and secondary amines, leading to 2,5-bis-amino derivatives (eq 7). 17 Spectroscopic studies have demonstrated that with aliphatic amines at least, the reaction proceeds via a one-electron oxidation of the amine. 18, 19 Chloranil has also been shown to induce the dimerization of diaryldiazomethanes through a reaction believed to involve prior addition across the quinone carbonyl group.…”

Section: -mentioning

confidence: 99%

Chloranil

Buckle¹,

Ohkubo

Fukuzumi

2016

Encyclopedia of Reagents for Organic Synthesis

View full text Add to dashboard Cite

“…The liberation of ethylene dicllloride on heating is characteristic of colllpounds bearing reactive p-chloroethylmercapto substituents (1). Infrared spectra showed the presence of a phenolic hydroxyl and this was confirllled by acetylation.…”

mentioning

confidence: 96%

REACTIONS OF 2,3,5,6-TETRAKIS(β-Hydroxyethylmercapto)-1,4-Hydroquinone AND RELATED COMPOUNDS

Kulka¹

1962

Can. J. Chem.

View full text Add to dashboard Cite

The treatment of chloranil (I) with alkali and 2-mercaptoethanol resulted not only in replacement of the chlorine atoms but also in reduction to form 2,3,5,6-tetrakis(β-hydroxyethylmercapto)-1,4-hydroquinone (II). The conditions for the preparation of 2,3,5,6-tetrakis(β-chloroethylmercapto)-1,4-hydroquinone (III) from II differed from those required for the preparation of a lower-melting compound (IV) from II by such a narrow margin that exact control of temperature and concentration were necessary in order to avoid erratic behavior in the preparation. The structure of the lower-melting compound has been established as 2,3-dihydro-5,7,8-tris(β-chloroethylmercapto)-6-hydroxy-1,4-benzoxathiin (IV) by analyses and cyclization reactions. The treatment of 2,3-dichloro-1,4-naphthoquinone (VIII) with 2-mercaptoethanol yielded 2,3-bis(β-hydroxyethylmercapto)-1,4-naphthoquinone (IX) and not the quinol as was the case with chloranil. The quinone (IX) could not be converted to 2,3-bis(β-chloroethylmercapto)-1,4-naphthoquinone by treatment with hydrogen chloride because under these conditions only 1,4-oxathio-5,10-anthraquinone (X) was formed. A mechanism for the formation of X which involves intramolecular addition, elimination, and cyclization is described.

show abstract

982. Syntheses of substituted amino-, aminovinyl-, and aminobutadienyl-p-quinones

Cited by 51 publications

References 0 publications

MO‐LCAO‐Calculations on polymethines. V. PPP‐type calculations and configuration analyses of simple prototype dyes in terms of molecular subsystems

MO‐LCAO‐Calculations on polymethines. V. PPP‐type calculations and configuration analyses of simple prototype dyes in terms of molecular subsystems

Chloranil

REACTIONS OF 2,3,5,6-TETRAKIS(β-Hydroxyethylmercapto)-1,4-Hydroquinone AND RELATED COMPOUNDS

Contact Info

Product

Resources

About