The Comparative Reactions of Forphin, 5-Bromoporphin, 2-Bromoporphin, and 5-Nitroporphin

Nudy, Louis R.; Schieber, C; Longo, Frederick R.; Agarwala, Vinod S.

doi:10.3987/r-1987-07-1797

Cited by 9 publications

(1 citation statement)

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“…For bromination of 5-nitroporphyrin it was expected that the nitro group would direct the bromine group to the 10 position. This was not the case as the only compound isolated was the 5,15-derivative; this is in line with the expectation that poorer selectivity is observed for stronger brominating agents [32].…”

Section: Reactivity S E Arsupporting

confidence: 70%

Porphyrin (porphine) — A neglected parent compound with potential

Senge

Davis

2010

J. Porphyrins Phthalocyanines

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ABSTRACT:Porphine is the parent compound of a family of biologically and chemically relevant compounds called porphyrins. The potential of these compounds is enormous and it would be advantageous to use the porphine (porphyrin) unit as a building block for the synthesis of diverse porphyrin complexes with a wide range of applications. However, despite first being synthesised over seventy years ago, porphine has not been utilized to its full extent due to low yield syntheses and poor solubility. Recent advances have now overcome many of these problems. The purpose of this review is to illustrate the advances made in porphine chemistry to illustrate the inherent potential of this simple compound. KEYWORDS:Porphine, porphyrin, metalloporphyrin, tetrapyrroles.

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Section: Reactivity S E Arsupporting

confidence: 70%

Porphyrin (porphine) — A neglected parent compound with potential

Senge

Davis

2010

J. Porphyrins Phthalocyanines

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Synthesis of Mono‐ and Disubstituted Porphyrins: A‐ and 5,10‐A₂‐Type Systems

Ryppa

Senge

Hatscher

et al. 2005

Chemistry A European J

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General syntheses have been developed for meso-substituted porphyrins with one or two substituents in the 5,10-positions and no beta substituents. 5-Substituted porphyrins with only one meso substituent are easily prepared by an acid-catalyzed condensation of dipyrromethane, pyrrole-2-carbaldehyde, and an appropriate aldehyde using a "[2+1+1]" approach. Similarly, 5,10-disubstituted porphyrins are accessible by simple condensation of unsubstituted tripyrrane with pyrrole and various aldehydes using a "[3+1]" approach. The yields for these reactions are low to moderate and additional formation of either di- or monosubstituted porphyrins due to scrambling of the intermediates is observed. However, the reactions can be performed quite easily and the desired target compounds are easily removed due to large differences in solubility. A complementary and more selective synthesis involves the use of organolithium reagents for S(N)Ar reactions. Reaction of in situ generated porphyrin (porphine) with 1.1-8 equivalents of RLi gave the monosubstituted porphyrins, while reaction with 3-6 equivalents of RLi gave the 5,10-disubstituted porphyrins in yields ranging from 43 to 90 %. These hitherto almost inaccessible compounds complete the series of different homologues of A-, 5,15-A(2)-, 5,10-A(2)-, A(3)-, and A(4)-type porphyrins and allow an investigation of the gradual influence of type, number, and regiochemical arrangement of substituents on the properties of meso-substituted porphyrins. They also present important starting materials for the synthesis of ABCD porphyrins and are potential synthons for supramolecular materials requiring specific substituent orientations.

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