Synthesis of oxygen analogues of the sulfchlorins

Iakovides, Panos; Smith, Kevin M.

doi:10.1016/s0040-4039(00)97486-0

Cited by 6 publications

(3 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The chlorin 11-H 2 31 bearing an annulated dihydrofuran ring is a homologue of sulfheme-C whereas chlorin–epoxide 11-H 2 33 is a homologue of sulfheme-A, as shown by comparing the structures in Schemes and . Mechanisms for the formation of the various pyrroline ring structures have been proposed. , The chlorin–epoxide 11-H 2 33 on stirring in the presence of neutral alumina rearranged to chlorin 11-H 2 31 in 40% yield. The absorption spectra of 11-H 2 31 and chlorin–epoxide 11-H 2 33 are shown in Figure .…”

Section: Cycloadditions With β-Vinylporphyrinsmentioning

confidence: 99%

“…383 Mechanisms for the formation of the various pyrroline ring structures have been proposed. 383,391 The chlorin−epoxide 11-H 2 33 on stirring in the presence of neutral alumina rearranged to chlorin 11-H 2 31 in 40% yield. The absorption spectra of 11-H 2 31 and chlorin− epoxide 11-H 2 33 are shown in Figure 33.…”

Section: Cycloadditions With β-Vinylporphyrinsmentioning

confidence: 99%

See 1 more Smart Citation

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

2016

View full text Add to dashboard Cite

Chlorophylls make Earth green, are the central constituents in the engine of photosynthesis, and not surprisingly have garnered immense attention. A chlorin, the core chromophore of a chlorophyll, is a dihydroporphyrin macrocycle that contains one pyrroline ring and three pyrrole rings. The dominant method for the synthesis of chlorins has entailed the derivatization of porphyrins. The present review covers the ostensibly simple conversion of porphyrins, regardless of synthetic or biological origin, to chlorins. The period covered encompasses the entire history since the beginnings of chlorin synthetic chemistry in the early 20th century through 2015. Representative transformations include hydrogenation, cycloaddition, annulation, and diverse "breaking and mending" approaches. Altogether, the synthesis of >1000 chlorins or chlorin-like compounds (containing >50 distinct pyrroline motifs) is described. Such diversity animates the question "what structural features are essential for a chlorin to resemble chlorophyll?" To begin to address the structure-spectrum relationship, > 250 absorption spectra are provided for representative structures. The synthesis and spectral properties of the vast collection of compounds described herein are expected to illuminate the scope to which synthetic chlorins can serve as surrogates for chlorophylls and be exploited in diverse ways.

show abstract

Section: Cycloadditions With β-Vinylporphyrinsmentioning

confidence: 99%

Section: Cycloadditions With β-Vinylporphyrinsmentioning

confidence: 99%

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

2016

View full text Add to dashboard Cite

show abstract

“…We made efforts to synthesize it and pursued a literature lead alleged to give an epoxide – only to find a completely unexpected ring‐opened product, still preserving a chlorin‐equivalent core (and lovely green color) 29. Eventually, the difficult case of epoxide was cracked by Smith’s group, using a Mitsunobu reaction 30. We are indebted to Fischer for keeping us busy for a century and then some!…”

Section: Hans Fischer Dipyrromethene Synthesis and His Far‐reachmentioning

confidence: 99%

Paul Rothemund and S. Ferguson MacDonald, and their Namesake Reactions – The Influence of the Fischer School on my Life in Porphyrin Chemistry

Chang

2015

Israel Journal of Chemistry

View full text Add to dashboard Cite

The Rothemund reaction and the MacDonald 2+2 condensation are two named reactions widely recognized in porphyrin syntheses. Yet not much has been written about the persons whose work paved the way to various porphyrins and porphyrinoids now realized. Paul Rothemund and S. Ferguson MacDonald both obtained their doctorate under Hans Fischer at Munich. Here I attempt to piece together the life stories of the two chemists, tracing back to the connections with the Fischer School, and giving the historical context to their namesake reactions. The pioneering discoveries of Fischer and his students, with later modifications, have become standard methods in the modern era for the synthesis of sizable quantities of porphyrins and porphyrinoids employed for enzyme models, catalysts, drugs, sensors, and building blocks of materials and biomedical research. This essay highlights the pioneers’ achievements, renders history relevant, and recounts the influence they had on my research.

show abstract

Unerwartete oxidative Ringöffnung eines (Octadehydrocorrinato)nickel(II)‐Salzes zu einem Chlorophin‐Derivat

Chang

Chern

et al. 1992

Angewandte Chemie

View full text Add to dashboard Cite

Ein Tetraazamakrocyclus aus drei Pyrroleinheiten und einem ankondensierten Furanring – „Furochlorophin”︁ – umgibt das NiII‐Ion in 1 Dieses 18 π‐Elektronensystem mit Chlorin‐Grundstruktur bildet sich überraschend einfach bei der Thermolyse von (Octadehydrocorrinato)nickel(II)‐chlorid. Diese Synthese dürfte nicht nur der Corrinoidchemie neue Impulse geben; die Absorptionscharakteristka des Metallkomplexes und der freien Base machen diese Verbindung auch für Anwendungen in der photodynamischen Krebstherapie interessant.

show abstract

Synthesis of oxygen analogues of the sulfchlorins

Cited by 6 publications

References 15 publications

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins

Paul Rothemund and S. Ferguson MacDonald, and their Namesake Reactions – The Influence of the Fischer School on my Life in Porphyrin Chemistry

Unerwartete oxidative Ringöffnung eines (Octadehydrocorrinato)nickel(II)‐Salzes zu einem Chlorophin‐Derivat

Contact Info

Product

Resources

About