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Cammidge, A. N. 
ORCID: https://orcid.org/0000-0001-7912-4310 and Ozturk, O.
(2002)
Selective synthesis of meso-naphthylporphyrins.
The Journal of Organic Chemistry, 67 (21).
pp. 7457-7464.
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 |
| Depositing User: | Rachel Smith |
| Date Deposited: | 09 May 2011 14:52 |
| Last Modified: | 12 May 2023 09:30 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/30060 |
| DOI: | 10.1021/jo0260488 |
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