Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX

The total synthesis of meso-monoaryl protoporphyrins (1) and (2) using a MacDonald type [2+2] condensation is described. In this method a bisformyl dipyrrylmethane is treated with a biscarboxydipyrrylmethane. Attempts to obtain the δ-meso-monoaryl protoporphyrin (7) by the a,c-biladiene method faile...

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Detalles Bibliográficos
Autores principales: Robinsohn, A.E., Maier, M.S., Buldain, G.Y.
Formato: JOUR
Materias:
macrocyclic compound
phenyl group
protoporphyrin
pyridine derivative
article
conformation
molecular model
polymerization
structure analysis
synthesis
technique
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_03855414_v53_n10_p2127_Robinsohn
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling todo:paper_03855414_v53_n10_p2127_Robinsohn2023-10-03T15:33:43Z Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX Robinsohn, A.E. Maier, M.S. Buldain, G.Y. macrocyclic compound phenyl group protoporphyrin pyridine derivative article conformation molecular model polymerization structure analysis synthesis technique The total synthesis of meso-monoaryl protoporphyrins (1) and (2) using a MacDonald type [2+2] condensation is described. In this method a bisformyl dipyrrylmethane is treated with a biscarboxydipyrrylmethane. Attempts to obtain the δ-meso-monoaryl protoporphyrin (7) by the a,c-biladiene method failed as it could not be prepared starting from its tripyrrene precursor. The synthesis of the latter compound is described. Molecular modeling studies allowed us to find the most favorable conformations for compounds (1) and (2). In both porphyrins, the exocyclic phenyl group adopts a noncoplanar disposition relative to the plane of the macrocycle. In porphyrin (2) the macrocycle is nearly planar while nonplanar saddle conformation was obtained for porphyrin (1). Fil:Maier, M.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_03855414_v53_n10_p2127_Robinsohn
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic macrocyclic compound
phenyl group
protoporphyrin
pyridine derivative
article
conformation
molecular model
polymerization
structure analysis
synthesis
technique
spellingShingle macrocyclic compound
phenyl group
protoporphyrin
pyridine derivative
article
conformation
molecular model
polymerization
structure analysis
synthesis
technique
Robinsohn, A.E.
Maier, M.S.
Buldain, G.Y.
Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX
topic_facet macrocyclic compound
phenyl group
protoporphyrin
pyridine derivative
article
conformation
molecular model
polymerization
structure analysis
synthesis
technique
description The total synthesis of meso-monoaryl protoporphyrins (1) and (2) using a MacDonald type [2+2] condensation is described. In this method a bisformyl dipyrrylmethane is treated with a biscarboxydipyrrylmethane. Attempts to obtain the δ-meso-monoaryl protoporphyrin (7) by the a,c-biladiene method failed as it could not be prepared starting from its tripyrrene precursor. The synthesis of the latter compound is described. Molecular modeling studies allowed us to find the most favorable conformations for compounds (1) and (2). In both porphyrins, the exocyclic phenyl group adopts a noncoplanar disposition relative to the plane of the macrocycle. In porphyrin (2) the macrocycle is nearly planar while nonplanar saddle conformation was obtained for porphyrin (1).
format JOUR
author Robinsohn, A.E.
Maier, M.S.
Buldain, G.Y.
author_facet Robinsohn, A.E.
Maier, M.S.
Buldain, G.Y.
author_sort Robinsohn, A.E.
title Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX
title_short Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX
title_full Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX
title_fullStr Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX
title_full_unstemmed Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX
title_sort total synthesis and conformational analysis of monophenyl substituted protoporphyrins ix
url http://hdl.handle.net/20.500.12110/paper_03855414_v53_n10_p2127_Robinsohn
work_keys_str_mv AT robinsohnae totalsynthesisandconformationalanalysisofmonophenylsubstitutedprotoporphyrinsix
AT maierms totalsynthesisandconformationalanalysisofmonophenylsubstitutedprotoporphyrinsix
AT buldaingy totalsynthesisandconformationalanalysisofmonophenylsubstitutedprotoporphyrinsix
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