Artículo
Intra- vs inter-molecular electron transfer processes in C[sbnd]N bond forming reactions. Photochemical, photophysical and theoretical study of 2′-halo-[1,1′-biphenyl]-2-amines
Guerra, Walter Damián
; Buden, Maria Eugenia
; Barolo, Silvia Maricel
; Rossi, Roberto Arturo
; Pierini, Adriana Beatriz
Fecha de publicación:
12/2016
Editorial:
Pergamon-Elsevier Science Ltd
Revista:
Tetrahedron
ISSN:
0040-4020
Idioma:
Inglés
Tipo de recurso:
Artículo publicado
Clasificación temática:
Resumen
N-Arylation reaction is obtained when 2′-halo-[1,1′-biphenyl]-2-amines are irradiated in basic medium. On the basis of photochemical, photophysical experiments and computational studies we propose that carbazoles are formed by intermolecular electron transfer via SRN1 mechanism. In general, biphenylamines with an EDG like Me or OMe behave in the same way as H giving both, cyclized and reduced products. On the other hand, biphenylamines containing EWG like CN, COOEt or CF3gave only the corresponding carbazole. Herein, we report for the first time the chain length for the propagation cycle of intramolecular SRN1 reactions and explain that differences in the distribution of products suggest differences regarding the overall mechanism involved.
Palabras clave:
Arylation Reaction
,
Electron Transfer
,
Photochemical
,
Radical Anions
,
Srn1
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Articulos(INFIQC)
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Articulos de INST.DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Citación
Guerra, Walter Damián; Buden, Maria Eugenia; Barolo, Silvia Maricel; Rossi, Roberto Arturo; Pierini, Adriana Beatriz; Intra- vs inter-molecular electron transfer processes in C[sbnd]N bond forming reactions. Photochemical, photophysical and theoretical study of 2′-halo-[1,1′-biphenyl]-2-amines; Pergamon-Elsevier Science Ltd; Tetrahedron; 72; 48; 12-2016; 7796-7804
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