Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

Mathias O. Senge; Steffen Runge; Marcus Speck; Karin Ruhlandt-Senge

doi:10.1016/S0040-4020(00)00823-1

Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

Mathias O. Senge, Steffen Runge, Marcus Speck, Karin Ruhlandt-Senge

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

53 Scopus citations

Abstract

Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldehyde with pyrrole allows the isolation and structural characterization of stable porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydroporphyrins) as intermediates of porphyrin synthesis. Crystal structures reveal the importance of the absolute configuration at the sp³-hybridized centers for the oxidation and stability of these (bio)synthetic intermediates. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	8927-8932
Number of pages	6
Journal	Tetrahedron
Volume	56
Issue number	45
DOIs	https://doi.org/10.1016/S0040-4020(00)00823-1
State	Published - Nov 3 2000

Keywords

Hydroporphyrins
Porphodimethenes
Porphomethenes
Porphyrins and analogues
Pyrroles
Silver porphyrins
Steric effects

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(00)00823-1

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title = "Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole",

abstract = "Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldehyde with pyrrole allows the isolation and structural characterization of stable porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydroporphyrins) as intermediates of porphyrin synthesis. Crystal structures reveal the importance of the absolute configuration at the sp3-hybridized centers for the oxidation and stability of these (bio)synthetic intermediates. (C) 2000 Elsevier Science Ltd.",

keywords = "Hydroporphyrins, Porphodimethenes, Porphomethenes, Porphyrins and analogues, Pyrroles, Silver porphyrins, Steric effects",

author = "Senge, {Mathias O.} and Steffen Runge and Marcus Speck and Karin Ruhlandt-Senge",

note = "Funding Information: This work was supported by grants from the Deutsche Forschungsgemeinschaft (Se543/2-5 and Heisenberg fellowship /3-2) and the Fonds der Chemischen Industrie. We are indebted to the Schering AG (Berlin) and the UC Davis Crystallographic Facility (M. M. Olmstead, director) for their support. ",

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doi = "10.1016/S0040-4020(00)00823-1",

language = "English (US)",

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pages = "8927--8932",

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TY - JOUR

T1 - Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

AU - Senge, Mathias O.

AU - Runge, Steffen

AU - Speck, Marcus

AU - Ruhlandt-Senge, Karin

N1 - Funding Information: This work was supported by grants from the Deutsche Forschungsgemeinschaft (Se543/2-5 and Heisenberg fellowship /3-2) and the Fonds der Chemischen Industrie. We are indebted to the Schering AG (Berlin) and the UC Davis Crystallographic Facility (M. M. Olmstead, director) for their support.

PY - 2000/11/3

Y1 - 2000/11/3

N2 - Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldehyde with pyrrole allows the isolation and structural characterization of stable porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydroporphyrins) as intermediates of porphyrin synthesis. Crystal structures reveal the importance of the absolute configuration at the sp3-hybridized centers for the oxidation and stability of these (bio)synthetic intermediates. (C) 2000 Elsevier Science Ltd.

AB - Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldehyde with pyrrole allows the isolation and structural characterization of stable porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydroporphyrins) as intermediates of porphyrin synthesis. Crystal structures reveal the importance of the absolute configuration at the sp3-hybridized centers for the oxidation and stability of these (bio)synthetic intermediates. (C) 2000 Elsevier Science Ltd.

KW - Hydroporphyrins

KW - Porphodimethenes

KW - Porphomethenes

KW - Porphyrins and analogues

KW - Pyrroles

KW - Silver porphyrins

KW - Steric effects

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U2 - 10.1016/S0040-4020(00)00823-1

DO - 10.1016/S0040-4020(00)00823-1

M3 - Article

AN - SCOPUS:0034602318

SN - 0040-4020

VL - 56

SP - 8927

EP - 8932

JO - Tetrahedron

JF - Tetrahedron

IS - 45

ER -

Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

Abstract

Keywords

ASJC Scopus subject areas

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