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Synlett 1990; 1990(5): 235-244
DOI: 10.1055/s-1990-21049
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1-Bromo-19-Methylbiladienes-ac; Useful Precursors to Porphyrins

Tilak P. Wijesekera* , David Dolphin
  • *Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Y6
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Publication Date:
08 March 2002 (online)

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The use of 1-bromo-19-methylbiladienes-ac in the synthesis of porphyrins is described. The stepwise construction of the linear tetrapyrrole via 5′-unsubstituted 5-methyldipyrromethenes and 5′-bromo -5-bromomethyldipyrromethenes as well as improvements and limitations in methodology are discussed. Several examples of its successful application are presented. 1. Introduction 2. Linear Tetrapyrroles 2.1. Bilenes-b 2.2. Biladienes-ac 3. 1-Bromo-19methylbiladienes-ac and Porphyrins Therefrom 3.1. 5′-Unsubstituted 5-Methyldipyrromethenes 3.2. 5′-Bromo-5-bromomethyldipyrromethenes 3.3. Porphyrin Synthesis 4. Applications 4.1. Mesoporphyrin II and Etioporphyrin III 4.2. Covalently Linked Dimeric Porphyrins 4.3. β-Unsubstituted β′-Monovinylporphyrin 4.4. A,C-Divinylporphyrins 4.5. Uroporphyrins I and III 5. Conclusion