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Synthesis 1994; 1994(9): 949-952
DOI: 10.1055/s-1994-25611
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Synthese von Bicyclo[2.2.1]hepta-2,5-dienyl-substituierten Porphyrinen

Frank Ludley* , Eberhard Breitmaier
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-53121 Bonn, Germany
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Publication Date:
17 September 2002 (online)

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Synthesis of Bicyclo[2.2.1]hepta-2,5-dienyl Substituted Porphyrins (E)- and (Z)-2-(p-Formylstyryl)-3- phenylbicyclo[2.2.1]hepta-2,5-dienes (7a,b) are prepared by Wittig alkenylation of 4-(1,3-dioxolan-2-yl)benzyltriphenylphosphonium bromide (4) and 3-phenylbicyclo[2.2.1]hepta-2,5-diene-2-carbaldehyde (5) in tetrahydrofuran to give (E)- and (Z)-2-[p-(1,3-dioxolan- 2-yl)styryl]-3-phenylbicyclo-[2.2.1]hepta-2,5-diene (6a,b) in 99% yield (E/Z-ratio 64:36) and the aldehydes 7a,b, after subsequent deprotection. Reaction of the aldehyde 7a with 3,3′-diethyl-4,4′- dimethyl-2,2′-dipyrrylmethane (8) affords porphyrine 1a in 60% yield, reactions of aldehydes 7a,b with pyrrole 9 give porphyrins 2a,b in 39 and 11% yield, respectively.