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

• Type: Article in International Scientific Journal
• Date: 2008

Authors

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

Journal

Title: European Journal of Organic Chemistry

Vol. 2008

Pages: 704-712

ISSN: 1434-193X

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 47 Citations

Scopus - 45 Citations

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9