Selective synthesis of meso-naphthylporphyrins

Cammidge, A. N. ORCID: and Ozturk, O. (2002) Selective synthesis of meso-naphthylporphyrins. The Journal of Organic Chemistry, 67 (21). pp. 7457-7464.

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A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the alpha,alpha-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of alpha,alpha-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.

Item Type: Article
Faculty \ School: Faculty of Science > School of Chemistry
UEA Research Groups: Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017)
Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Faculty of Science > Research Groups > Chemistry of Light and Energy
Depositing User: Rachel Smith
Date Deposited: 09 May 2011 14:52
Last Modified: 12 May 2023 09:30
DOI: 10.1021/jo0260488

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