Selective synthesis of meso-naphthylporphyrins

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

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Abstract

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
University of East Anglia > Faculty of Science > Research Groups > Synthetic Chemistry
Depositing User: Rachel Smith
Date Deposited: 09 May 2011 15:52
Last Modified: 25 Jul 2018 07:22
URI: https://ueaeprints.uea.ac.uk/id/eprint/30060
DOI: 10.1021/jo0260488

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