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dc.contributor.author
Bonesi, Sergio Mauricio  
dc.contributor.author
Dondi, Daniele  
dc.contributor.author
Protti, Stefano  
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Fagnoni, Maurizio  
dc.contributor.author
Albini, Angelo  
dc.date.available
2016-11-11T19:00:48Z  
dc.date.issued
2014-04  
dc.identifier.citation
Bonesi, Sergio Mauricio; Dondi, Daniele; Protti, Stefano; Fagnoni, Maurizio; Albini, Angelo; (Co)oxidation/cyclization processes upon irradiation of triphenylamine; Elsevier; Tetrahedron Letters; 55; 18; 4-2014; 2932–2935  
dc.identifier.issn
0040-4039  
dc.identifier.uri
http://hdl.handle.net/11336/8155  
dc.description.abstract
Abstract. 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.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Elsevier  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/  
dc.subject
Photooxidation  
dc.subject
Photocyclization  
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Phosphine Oxidation  
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Sulphide Oxidation  
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Química Orgánica  
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Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
(Co)oxidation/cyclization processes upon irradiation of triphenylamine  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2016-11-11T15:09:24Z  
dc.journal.volume
55  
dc.journal.number
18  
dc.journal.pagination
2932–2935  
dc.journal.pais
Países Bajos  
dc.journal.ciudad
Amsterdam  
dc.description.fil
Fil: Bonesi, Sergio Mauricio. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina  
dc.description.fil
Fil: Dondi, Daniele. Universita Di Pavia; Italia  
dc.description.fil
Fil: Protti, Stefano. Universita Di Pavia; Italia  
dc.description.fil
Fil: Fagnoni, Maurizio. Universita Di Pavia; Italia  
dc.description.fil
Fil: Albini, Angelo. Universita Di Pavia; Italia  
dc.journal.title
Tetrahedron Letters  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0040403914005073  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.tetlet.2014.03.086  

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