Porphyrins in Diels-Alder reactions. Improvements on the synthesis of barrelene-fused chlorins using microwave irradiation

• Type: Article in International Scientific Journal
• Date: 2005

Authors

Silva, AMG (Author) Other; Tome, AC (Author) Other; Neves, MGPMS (Author) Other; Cavaleiro, JAS (Author) Other; Kappe, CV (Author) Other

Journal

Title: Tetrahedron Letters

Vol. 46

Pages: 4723-4726

ISSN: 0040-4039

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 48 Citations

Scopus - 48 Citations

Other information

Authenticus ID: P-000-2CM

DOI: 10.1016/j.tetlet.2005.05.047

Abstract (EN): The microwave irradiation technique was applied to the Diels-Alder reaction of tetrakis(pentafluorophenyl)porphyrin with pentacene and naphthacene. Both reactions proceed within minutes to afford the corresponding monoadducts in 83% and 23% yield, respectively. When compared with the yields obtained under classical heating (22% and no reaction, respectively), this represents an impressive improvement of these reactions. Bisadducts (bacteriochlorins and isobacteriochlorins) are also obtained in the reaction with pentacene; these compounds are not formed under classical heating.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 4