Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Special issue | Vol 54, No. 2, 2001, pp.705-720
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)48
Preparation of Meso-unsubstituted Porphyrins Substituted with Mono- and Tetraformyl and Other Electron- withdrawing Groups

Yumiko Fumoto, Hidemitsu Uno, Takashi Murashima, and Noboru Ono*

*Department of Chemistry, Faculty of Science, Ehime University, Matsuyama 790-8577, Japan

Abstract

A meso-unsubstituted porphyrin having a formyl group was synthesized both from a mono(ethoxycarbonyl)porphyrin by reduction with LiAlH4 followed by oxidation with MnO2 and from a monocyanoporphyrin by reduction with DIBALH. The monoethoxycarbonyl and monocyanoporphyrins were prepared by the acid catalyzed mixed condensation of the corresponding 4-ethoxycarbonyl- and 4-cyano-2-(hydroxymethyl)pyrroles with 3-mesityl-4-methyl-2-(hydroxymethyl)pyrrole. A porphyrin with four formyl groups at the β-positions was prepared from ethyl 4-(dithiolan-2-yl)-3-methylpyrrole-2-carboxylate by the sequential treatment of LiAlH4, p-TsOH, and NBS. Cyclic voltammetry and UV-VIS spectroscopic analyses of these porphyrins revealed the highly electron-deficient property of the porphyrin chromophore.