The reactivity of the three isomeric methoxy-substituted N,N-dimethylanilines (N,N-dimethylanisidines) and ofN,N-dimethyl-2,6-dimethoxyaniline in the reduction with alkali metals in aprotic solvents was investigated.N,N-Dimethyl-p-methoxyaniline was found to be unreactive, while the other substrates underwent exclusive cleavage of carbon-oxygen bond(s), with the following order of reactivity: 2,6-dimethoxy >o-methoxy >m-methoxy >p-methoxy. Both the relative reactivity and the regioselectivity of cleavage (demethoxylationvs. demethylation) was found to parallel closely that of the corresponding di- and trimethoxysubstituted substrates. These results suggest that intermediates with different electron distribution or even different intermediates are involved in the reductive cleavage of aryl-oxygen and arylnitrogen bonds.

Electron-transfer-induced reductive dealkoxylation of alkyl aryl ethers. III. Reductive cleavage of methoxy-substitutedN,N-dimethylanilines (N,N-dimethylanisidines) / Azzena, Ugo Gavino; Pisano, Luisa; Dessanti, Francesca; Melloni, Giovanni. - In: ARKIVOC. - ISSN 1551-7004. - 2002:v(2002), pp. 181-188. [10.3998/ark.5550190.0003.520]

Electron-transfer-induced reductive dealkoxylation of alkyl aryl ethers. III. Reductive cleavage of methoxy-substitutedN,N-dimethylanilines (N,N-dimethylanisidines)

Azzena, Ugo Gavino
;
Pisano, Luisa
;
2002-01-01

Abstract

The reactivity of the three isomeric methoxy-substituted N,N-dimethylanilines (N,N-dimethylanisidines) and ofN,N-dimethyl-2,6-dimethoxyaniline in the reduction with alkali metals in aprotic solvents was investigated.N,N-Dimethyl-p-methoxyaniline was found to be unreactive, while the other substrates underwent exclusive cleavage of carbon-oxygen bond(s), with the following order of reactivity: 2,6-dimethoxy >o-methoxy >m-methoxy >p-methoxy. Both the relative reactivity and the regioselectivity of cleavage (demethoxylationvs. demethylation) was found to parallel closely that of the corresponding di- and trimethoxysubstituted substrates. These results suggest that intermediates with different electron distribution or even different intermediates are involved in the reductive cleavage of aryl-oxygen and arylnitrogen bonds.
2002
Electron-transfer-induced reductive dealkoxylation of alkyl aryl ethers. III. Reductive cleavage of methoxy-substitutedN,N-dimethylanilines (N,N-dimethylanisidines) / Azzena, Ugo Gavino; Pisano, Luisa; Dessanti, Francesca; Melloni, Giovanni. - In: ARKIVOC. - ISSN 1551-7004. - 2002:v(2002), pp. 181-188. [10.3998/ark.5550190.0003.520]
File in questo prodotto:
File Dimensione Formato  
Azzena_U_Articolo_2002_Electron.pdf

accesso aperto

Tipologia: Versione editoriale (versione finale pubblicata)
Licenza: Non pubblico (Accesso privato/ristretto)
Dimensione 112.69 kB
Formato Adobe PDF
112.69 kB Adobe PDF Visualizza/Apri

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11388/264979
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 7
  • ???jsp.display-item.citation.isi??? 8
social impact