2001
DOI: 10.1002/1521-3757(20010917)113:18<3547::aid-ange3547>3.0.co;2-z
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Multicarbocycle Formation Mediated by Arenoporphyrin 1,4-Diradicals: Synthesis of Picenoporphyrins

Abstract: Bergman‐Cyclisierung von 2,3‐Dialkinyl‐meso‐tetraphenylporphyrin und anschließende 1,4‐Diradikal‐vermittelte C‐C‐Kupplung zwischen benachbarten meso‐Phenylringen führten zur Bildung eines unerwarteten, an der Porphyrinperipherie anellierten Multicarbocyclus. Die Stammmoleküle (1; R=Bu, H, Ph) mit ausgedehntem π‐Elektronensystem werden beschrieben und werden, wegen ihrer [5]Phenacen‐Struktur, als Picenoporphyrine bezeichnet.

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Cited by 21 publications
(7 citation statements)
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“…The fifth and subsequent eliminations proceed with low efficiency, and the corresponding fragment peaks are minor compared to the peaks resulting from the first four eliminations (note the 10-fold intensity enhancement of the spectrum below m/z 890). It is, therefore, not surprising that literature precedence for the bulk-phase formation of o-,o=-linked phenyl groups in the solution phase are rare and involve only one phenyl group and two enclosed six-membered rings or one fiveand one six-membered ring [40,41]. Porphyrinoids containing direct ␤-to-o-linkages enclosing five-membered rings between the phenyl and the porphyrin macrocycle are also known, though their establishment follow different routes than presumed here [42,43].…”
Section: F Pp ϫ H]mentioning
confidence: 99%
“…The fifth and subsequent eliminations proceed with low efficiency, and the corresponding fragment peaks are minor compared to the peaks resulting from the first four eliminations (note the 10-fold intensity enhancement of the spectrum below m/z 890). It is, therefore, not surprising that literature precedence for the bulk-phase formation of o-,o=-linked phenyl groups in the solution phase are rare and involve only one phenyl group and two enclosed six-membered rings or one fiveand one six-membered ring [40,41]. Porphyrinoids containing direct ␤-to-o-linkages enclosing five-membered rings between the phenyl and the porphyrin macrocycle are also known, though their establishment follow different routes than presumed here [42,43].…”
Section: F Pp ϫ H]mentioning
confidence: 99%
“…Solid‐state thermal reactivity : Differential scanning calorimetry (DSC) has been shown to be a reliable tool for measuring Bergman cyclization temperatures of metalloenediyne structures in the solid state (absence of an H donor), and effectively correlates the temperature with the distance between the alkyne termini 7. 9b, 10b, 13, 17, 18 Solid‐state cyclization temperatures for 3 a–c all exhibit a major exothermic peak between 149 and 150 °C, which reveals that activation of all three tetraalkynyl derivatives occurs at a comparable temperature.…”
Section: Resultsmentioning
confidence: 99%
“…The thermal Bergman cyclization reaction of dialkynyl porphyrins was originally shown by Smith et al 7. to proceed in high yields (ca.…”
Section: Resultsmentioning
confidence: 99%
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“…John and Tour6 reported the formation of polyphenylenes using BC, while Grissom and Calkins7 demonstrated the tandem radical cyclization of enediynes with diverse alkenyl acceptors. Diradicals generated in a porphyrin network have been trapped with a neighboring aromatic ring (Smith and co‐workers,8a and Zaleski and co‐workers8b). Taking a cue from these results and the ortho effect reported by Alabugin and co‐workers,9 we studied the reactivity of aryl exomethylene N‐substituted cyclic enediynes of type A (Scheme ).…”
Section: Methodsmentioning
confidence: 99%