Chemical transformations of mono- and bis(buta-1,3-dien-1-yl)porphyrins: A new synthetic approach to mono- and dibenzoporphyrins

• Tipo: Artigo em Revista Científica Internacional
• Data: 2008

Autores

Silva, AMG (Autor) Outra; de Oliveira, KT (Autor) Outra; Faustino, MAF (Autor) Outra; Neves, MGPMS (Autor) Outra; Tome, AC (Autor) Outra; Silva, AMS (Autor) Outra; Cavaleiro, JAS (Autor) Outra; Brandao, P (Autor) Outra; Felix, V (Autor) Outra

Revista

Título: European Journal of Organic Chemistry

Vol. 2008

Páginas: 704-712

ISSN: 1434-193X

Editora: Wiley-Blackwell

Indexação

ISI Web of Knowledge - 47 Citações

Scopus - 45 Citações

Outras Informações

ID Authenticus: P-004-1Q3

DOI: 10.1002/ejoc.200700852

Abstract (EN): beta-Butadienyl- and beta,beta'-dibutadienylporphyrins were prepared by the Wittig reaction of beta-formyl- and beta,beta'-diformylmeso-tetraphenylporphyrins with allylic phosphorus ylide. Subsequent treatment of beta-butadienylporphyrin with dienophiles afforded the corresponding Diels-Alder adducts. In the absence of dienophiles, beta-butadienylporphyrin underwent electrocyclization, followed by oxidation, to give monobenzoporphyrin in good yield. Similarly, adjacent and opposite dibenzoporphyrins were successfully synthesized from adjacent and opposite beta,beta'-dibutadienylporphyrins, respectively. This is the first report of electrocyclization of beta-butadienylporphyrins. The structures of mono- and dibenzoporphyrin nickel complexes, as well as of a Diels-Alder adduct, were determined by single-crystal X-ray diffraction; a strong distortion from the planarity of the porphyrin core was observed. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 9