Synthesis of highly substituted meso-tetraarylporphyrins |
| |
Authors: | Stanis?aw Ostrowski Agnieszka Mikus |
| |
Affiliation: | a Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland b Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, 01-224 Warszawa, Poland |
| |
Abstract: | meso-Tetraphenylporphyrin (and its derivatives), in the reaction with fuming yellow nitric acid (d=1.53), form either 5-(4-nitroaryl)-10,15,20-triarylporphyrin, 5,10-bis(4-nitroaryl)-15,20-diarylporphyrin, or 5,10,15-tris(4-nitroaryl)-20-arylporphyrin, depending on the reaction temperature (0-20 °C), amounts of the acid used, and reaction time. The above nitroporphyrins react, in the presence of a base (t-BuOK) at 0 °C, with carbanions (which bear nucleophugal groups at the carbanionic center: −CH(Cl)SO2Tol, −CH(Br)SO2Tol, and −CH(Cl)SO2NMe2), leading to the nucleophilic substitution of hydrogen in one or more of the meso-nitroaryl rings. By this route, the preparation of the highly substituted ‘synthetic’ porphyrins (bearing up to ten O-, N-, Cl-, or C-substituents) was demonstrated. |
| |
Keywords: | meso-Tetraarylporphyrins Nitration Carbanions Nucleophilic substitution of hydrogen |
本文献已被 ScienceDirect 等数据库收录! |
|