Selective synthesis of meso-naphthylporphyrins.
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.
Cammidge
Andrew N
AN
School of Chemical Sciences, University of East Anglia, Norwich NR4 7TJ UK. a.cammidge@uea.ac.uk
Oztürk
Orhan
O
D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D011166:Porphyrins / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007202:Indicators and Reagents; D009284:Naphthols; D011166:Porphyrins