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dc.contributor.author
Gazzano, Emiliano R. A.
dc.contributor.author
Lazaro Martinez, Juan Manuel
dc.contributor.author
Buldain, Graciela Yolanda
dc.date.available
2018-06-04T20:45:51Z
dc.date.issued
2016-12
dc.identifier.citation
Gazzano, Emiliano R. A.; Lazaro Martinez, Juan Manuel; Buldain, Graciela Yolanda; A New Look at the Halogenation of Porphyrins; Bentham Science Publishers; Current Organic Chemistry; 21; 2; 12-2016; 177-182
dc.identifier.issn
1385-2728
dc.identifier.uri
http://hdl.handle.net/11336/47235
dc.description.abstract
The present study describes the selective halogenation at the β - or meso-position of the porphyrin macrocycle. The reactions of deuteroporphyrin IX dimethyl ester, mesoporphyrin III dimethyl ester and their Cu(II) and Ni(II) complexes with N-bromosuccinimide or phenylselenyl chloride were investigated. It could be observed that when the bromination of deuteroporphyn IX dimethyl ester using NBS took place, the isolated products were the result of an electrophilic substitution in β-free porphyrin ring positions. Employing the same reagent for halogenating mesoporphyrin III dimethyl ester, which does not possess β-free position, different derivatives were obtained from the allylic bromination of the ethyl side chain. When phenylselenyl chloride was used as halogenating agent with deuteroporphyn IX dimethyl ester or its Cu(II) complex, in both cases the replacement of β-free hydrogen atoms by phenylselenyl group was afforded. When the Ni(II) mesoporphyrin III dimethyl ester was used the desired and selective replacement of meso hydrogen atoms of aromatic ring by chlorine atoms was obtained. The structural assignment of the porphyrin derivatives thus obtained was performed by high-resolution mass spectrometry and detailed analysis of the NMR spectra.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Bentham Science Publishers
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Halogenacion
dc.subject
Deuteroporfirina Ix Dimetil Ester
dc.subject
Mesoporfirina Iii Dimetil Ester
dc.subject.classification
Otras Ciencias Químicas
dc.subject.classification
Ciencias Químicas
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CIENCIAS NATURALES Y EXACTAS
dc.title
A New Look at the Halogenation of Porphyrins
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-06-04T17:04:15Z
dc.journal.volume
21
dc.journal.number
2
dc.journal.pagination
177-182
dc.journal.pais
Estados Unidos
dc.journal.ciudad
Oak Park
dc.description.fil
Fil: Gazzano, Emiliano R. A.. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina
dc.description.fil
Fil: Lazaro Martinez, Juan Manuel. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.description.fil
Fil: Buldain, Graciela Yolanda. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
dc.journal.title
Current Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://www.eurekaselect.com/145720
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.2174/1385272820666160922154159
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