Journal
TETRAHEDRON
Volume 72, Issue 48, Pages 7796-7804Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2016.08.051
Keywords
Electron transfer; Photochemical; Arylation reaction; S(RN)1; Radical anions
Categories
Funding
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET) [PIP-2012]
- Secretaria de Ciencia y Tecnologia, Universidad Nacional de Cordoba (SECT)
- Agencia Nacional de Promocion Cientifica y Tecnica (ANPCyT) [PICT 2012-2303]
- CONICET
Ask authors/readers for more resources
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 S(RN)1 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 CF3 gave only the corresponding carbazole. Herein, we report for the first time the chain length for the propagation cycle of intramolecular S(RN)1 reactions and explain that differences in the distribution of products suggest differences regarding the overall mechanism involved. (C) 2016 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available