(Co)oxidation/cyclization processes upon irradiation of triphenylamine

Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy...

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Autor principal:	Bonesi, Sergio Mauricio
Publicado:	2014
Materias:	Phosphine oxidation Photocyclization of triphenylamine Photooxidation Sulfide oxidation amine hydrogen hydroperoxide triphenylamine unclassified drug article calculation cooxidation cyclization density functional theory irradiation oxidation photooxidation
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v55_n18_p2932_Bonesi http://hdl.handle.net/20.500.12110/paper_00404039_v55_n18_p2932_Bonesi
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00404039_v55_n18_p2932_Bonesi
record_format	dspace
spelling	paper:paper_00404039_v55_n18_p2932_Bonesi2023-06-08T15:04:29Z (Co)oxidation/cyclization processes upon irradiation of triphenylamine Bonesi, Sergio Mauricio Phosphine oxidation Photocyclization of triphenylamine Photooxidation Sulfide oxidation amine hydrogen hydroperoxide triphenylamine unclassified drug article calculation cooxidation cyclization density functional theory irradiation oxidation photooxidation Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides. © 2014 Elsevier Ltd. All rights reserved. Fil:Bonesi, S.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2014 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v55_n18_p2932_Bonesi http://hdl.handle.net/20.500.12110/paper_00404039_v55_n18_p2932_Bonesi
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Phosphine oxidation Photocyclization of triphenylamine Photooxidation Sulfide oxidation amine hydrogen hydroperoxide triphenylamine unclassified drug article calculation cooxidation cyclization density functional theory irradiation oxidation photooxidation
spellingShingle	Phosphine oxidation Photocyclization of triphenylamine Photooxidation Sulfide oxidation amine hydrogen hydroperoxide triphenylamine unclassified drug article calculation cooxidation cyclization density functional theory irradiation oxidation photooxidation Bonesi, Sergio Mauricio (Co)oxidation/cyclization processes upon irradiation of triphenylamine
topic_facet	Phosphine oxidation Photocyclization of triphenylamine Photooxidation Sulfide oxidation amine hydrogen hydroperoxide triphenylamine unclassified drug article calculation cooxidation cyclization density functional theory irradiation oxidation photooxidation
description	Irradiation of triphenylamine (Ph3N) in nitrogen-flushed solution leads to 9-phenylcarbazole and two tetrahydroderivatives (1,2,3,4- and 1,2,7,8-) via disproportionation of the corresponding 4a,4b-dihydrocarbazole. In oxygen-equilibrated solution oxidative cyclization occurs through the intermediacy of a triplet peroxy diradical, which either abstracts a hydrogen atom intramolecularly or (mainly) cleaves back to the reagents. The role of the key intermediates is supported by DFT calculations and by trapping by triarylphosphines (that are thus efficiently oxidized, while preventing the cyclization of Ph3N). The hydroperoxide, on the other hand, causes inefficient co-oxidation of sulfides. © 2014 Elsevier Ltd. All rights reserved.
author	Bonesi, Sergio Mauricio
author_facet	Bonesi, Sergio Mauricio
author_sort	Bonesi, Sergio Mauricio
title	(Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_short	(Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_full	(Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_fullStr	(Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_full_unstemmed	(Co)oxidation/cyclization processes upon irradiation of triphenylamine
title_sort	(co)oxidation/cyclization processes upon irradiation of triphenylamine
publishDate	2014
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404039_v55_n18_p2932_Bonesi http://hdl.handle.net/20.500.12110/paper_00404039_v55_n18_p2932_Bonesi
work_keys_str_mv	AT bonesisergiomauricio cooxidationcyclizationprocessesuponirradiationoftriphenylamine
_version_	1768541884168273920

(Co)oxidation/cyclization processes upon irradiation of triphenylamine

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