Heterocyclische Azidiniumsalze in der präparativen Chemie

Die Reaktivität von «harten» und «weichen» Nucleophilen (Hydroxid, Methoxid, Dimethylamin, 2‐Imino‐3‐äthyl‐benzthiazolin, Triphenylphosphin, Carbanionen, Azid, Cyanid, Arylsulfinat, 3‐Äthyl‐benzthiazolin‐2‐yliden, 3‐Methyl‐benzthiazolinon‐(2)‐hydrazon) gegenüber dem ambidenten elektrophilen 2‐Azido‐3‐äthyl‐benzthiazolium‐Ion wird untersucht. Das reaktive Verhalten lässt sich mit Hilfe des HSAB‐Konzepts von Pearson deuten.

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Synthesis, Structure and Photochemical Properties of 4, 4′, 7, 7′‐Tetra‐substituted 1,1′, 3,3′‐Tetraethylbenzimidazolotriazatrimethine Cyanines

Naef

Balli

1978

Helvetica Chimica Acta

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NaN&F quaternisation of 1 by triethyloxonium tetrafluoroborate gave the symmetrical 2-chloro-1,3-diethylbenzimidazoliurn salts 7 in good yields, substitution of chloride by azide ion afforded the azidinium salts 8 which, without further purification, were converted into the final products 6a-6d through reaction with sodium azide in dimethylformamide. The mechanism of the latter reaction is well documented [ 191, Electron absorption spectra. -Method.All absorption spectra of dyes 6a-6d were taken in ethanoUmethanol/2-propanol (90: 5 : 5 ) at concentrations of about moV1. It was controlled that Beer-Lambert's law was observed.Results and discussion. A comparison of the absorption spectra of the analogous trimethine cyanine 9 [20] and 6a shows a strongly hypsochromic shift from 485 nm [20] to 435 nm (Tablel), which was interpreted by Balli [2] as a superposition of 2

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Heterocyclische Azidiniumsalze in der präparativen Chemie

Cited by 4 publications

References 7 publications

Azidiniumsalze. 9.Mitteilung [1]. Struktur‐Reaktivitäts‐Beziehungen in Serien quartärer N‐Heteroaromaten: Aciditätskonstanten von 2‐Amino‐cyclimonium‐Ionen als σ_Het‐Konstanten

Azidiniumsalze. 9.Mitteilung [1]. Struktur‐Reaktivitäts‐Beziehungen in Serien quartärer N‐Heteroaromaten: Aciditätskonstanten von 2‐Amino‐cyclimonium‐Ionen als σ_Het‐Konstanten

Azidiniumsalze. 12. Mitteilung [1]. Das ambidente reaktive Verhalten des 2‐Azido‐3‐äthyl‐benzthiazolium‐Ions gegenüber Nucleophilen

Synthesis, Structure and Photochemical Properties of 4, 4′, 7, 7′‐Tetra‐substituted 1,1′, 3,3′‐Tetraethylbenzimidazolotriazatrimethine Cyanines

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Heterocyclische Azidiniumsalze in der präparativen Chemie

Cited by 4 publications

References 7 publications

Azidiniumsalze. 9.Mitteilung [1]. Struktur‐Reaktivitäts‐Beziehungen in Serien quartärer N‐Heteroaromaten: Aciditätskonstanten von 2‐Amino‐cyclimonium‐Ionen als σHet‐Konstanten

Azidiniumsalze. 9.Mitteilung [1]. Struktur‐Reaktivitäts‐Beziehungen in Serien quartärer N‐Heteroaromaten: Aciditätskonstanten von 2‐Amino‐cyclimonium‐Ionen als σHet‐Konstanten

Azidiniumsalze. 12. Mitteilung [1]. Das ambidente reaktive Verhalten des 2‐Azido‐3‐äthyl‐benzthiazolium‐Ions gegenüber Nucleophilen

Synthesis, Structure and Photochemical Properties of 4, 4′, 7, 7′‐Tetra‐substituted 1,1′, 3,3′‐Tetraethylbenzimidazolotriazatrimethine Cyanines

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Product

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Azidiniumsalze. 9.Mitteilung [1]. Struktur‐Reaktivitäts‐Beziehungen in Serien quartärer N‐Heteroaromaten: Aciditätskonstanten von 2‐Amino‐cyclimonium‐Ionen als σ_Het‐Konstanten

Azidiniumsalze. 9.Mitteilung [1]. Struktur‐Reaktivitäts‐Beziehungen in Serien quartärer N‐Heteroaromaten: Aciditätskonstanten von 2‐Amino‐cyclimonium‐Ionen als σ_Het‐Konstanten