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...
Guardado en:
| Autor principal: | |
|---|---|
| Publicado: |
2000
|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03855414_v53_n10_p2127_Robinsohn http://hdl.handle.net/20.500.12110/paper_03855414_v53_n10_p2127_Robinsohn |
| Aporte de: |
| id |
paper:paper_03855414_v53_n10_p2127_Robinsohn |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_03855414_v53_n10_p2127_Robinsohn2023-06-08T15:40:51Z Total synthesis and conformational analysis of monophenyl substituted protoporphyrins IX Maier, Marta Silvia 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. 2000 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03855414_v53_n10_p2127_Robinsohn 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 Maier, Marta Silvia 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). |
| author |
Maier, Marta Silvia |
| author_facet |
Maier, Marta Silvia |
| author_sort |
Maier, Marta Silvia |
| 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 |
| publishDate |
2000 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03855414_v53_n10_p2127_Robinsohn http://hdl.handle.net/20.500.12110/paper_03855414_v53_n10_p2127_Robinsohn |
| work_keys_str_mv |
AT maiermartasilvia totalsynthesisandconformationalanalysisofmonophenylsubstitutedprotoporphyrinsix |
| _version_ |
1768541658161348608 |