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Expansion of a Pyrrole in meso‐Tetraphenylporphyrin to a Pyrazine Imide Moiety Using a Beckmann Rearrangement
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Titel: |
Expansion of a Pyrrole in meso‐Tetraphenylporphyrin to a Pyrazine Imide Moiety Using a Beckmann Rearrangement |
In: | European Journal of Organic Chemistry, 2013, 2013, 18, S. 3876-3884 |
veröffentlicht: |
Wiley
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Umfang: | 3876-3884 |
ISSN: |
1434-193X 1099-0690 |
DOI: | 10.1002/ejoc.201300274 |
Zusammenfassung: | <jats:title>Abstract</jats:title><jats:p>The group 10 metal complexes of β,β′‐dioxoporphyrin monooxime <jats:bold>10</jats:bold>M (M = Ni<jats:sup>II</jats:sup>, Pd<jats:sup>II</jats:sup>, Pt<jats:sup>II</jats:sup>) are susceptible to a Beckmann rearrangement to produce the corresponding ring‐expanded metallopyrazinoporphyrin imides <jats:bold>11</jats:bold>M in good yields. These chromophores possess metallochlorin‐like optical properties. Demetalation of the Ni<jats:sup>II</jats:sup> complex furnishes the free‐base porphyrinoid <jats:bold>11</jats:bold>, which possesses a porphyrin‐like optical spectrum. The monooximes are ultimately derived from <jats:italic>meso</jats:italic>‐tetraphenylporphyrin, and the formal replacement of the porphyrin β,β′‐double bond by an imide functionality is thus demonstrated. The imide functionality serves as a synthetic handle for further modification of the chromophore.</jats:p> |
Format: | E-Article |
Quelle: | Wiley (CrossRef) |
Sprache: | Englisch |