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Mutual Interconversion of the Chromophoric Systems of Porphyrinogen and Isobacteriochlorin^†

dipl. Naturwiss. ETH Christof Angst

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

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Dr. Masahiro Kajiwara,

Dr. Masahiro Kajiwara

Shiseido Laboratories, 1050 Nippa-cho, Kohoku-ku, Yokohama 223 (Japan)

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Dr. Engelbert Zass,

Dr. Engelbert Zass

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

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Prof. Dr. Albert Eschenmoser,

Corresponding Author

Prof. Dr. Albert Eschenmoser

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)Search for more papers by this author

dipl. Naturwiss. ETH Christof Angst,

dipl. Naturwiss. ETH Christof Angst

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

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Dr. Masahiro Kajiwara,

Dr. Masahiro Kajiwara

Shiseido Laboratories, 1050 Nippa-cho, Kohoku-ku, Yokohama 223 (Japan)

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Dr. Engelbert Zass,

Dr. Engelbert Zass

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

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Prof. Dr. Albert Eschenmoser,

Corresponding Author

Prof. Dr. Albert Eschenmoser

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

Laboratorium für organische Chemie, Eidgenössische Technische Hoschschule ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)Search for more papers by this author

First published: February 1980

https://doi.org/10.1002/anie.198001401

Citations: 26

^†

The Chemistry of Hexahydroporphyrins, Part 1. This work was supported by the Swiss National Science Foundation.

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Reactions of hexahydroporphyrins in the absence of air are strongly influenced by metal ions. Thus the tetrapyrrolic porphyrinogen (1), R = C₂H₅, reacts in the presence of Co²⁺ via several steps, including isobacteriochlorins (2), to give the hemicorrinoid dipyrrolic compounds (3). These are tautomers of (1). In the presence of Ni²⁺, (1) form complexes of the new hemicorrinoid-pyrromethenic system (4). ttct-(4) and tttt-(4) were characterized by their spectra and also by X-ray structure analysis. (The species ttt-(2), ttt-(3), and tttt-(4) likewise formed are not included in the scheme below.)

References

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8 The chlorin mixture, only sparingly soluble in ether/methanol, was isolated by crystallization and separated into homogeneous diastereomers by HPLC (neutral alumina, pentane/dimethoxyethane/triethylamine 1000:30:15, no exclusion of oxygen). These diastereomers were identified by comparison of the UV/VIS, ¹H/¹³C-NMR, MS, and IR spectra with those of reference material prepared according to [11a].
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16 The accompanying bis-dehydrogenation presumably occurs via disproportionation, cf. [7].
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Volume19, Issue2

February 1980

Pages 140-141

Mutual Interconversion of the Chromophoric Systems of Porphyrinogen and Isobacteriochlorin^†

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Mutual Interconversion of the Chromophoric Systems of Porphyrinogen and Isobacteriochlorin†

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Mutual Interconversion of the Chromophoric Systems of Porphyrinogen and Isobacteriochlorin^†