Rothemund-Lindsey Porphyrin Synthesis

• General Characteristics

Meso-substituted porphyrins are synthesized by condensation of aldehydes and pyrroles followed by oxidation. The early methods needed forcing conditions but the improvements made by Lindsey allow this reaction to take place at room temperature. High dilution conditions are necessary.

By reacting preformed dipyrromethanes derived from one aldehyde with another kind of aldehyde, it is possible to synthesize C2-symmetric porphyrin derivatives.

• General References

•  Rothemund, P. J. Am. Chem. Soc. 1935, 57, 2010. doi:10.1021/ja01313a510
•  Rothemund, P. J. Am. Chem. Soc. 1936, 58, 625. doi:10.1021/ja01295a027
•  Adler, A.D.; Longo, F. R.; Shergalis, W. J. Am. Chem. Soc. 1964, 86, 3145. DOI: 10.1021/ja01069a035
•  Adler, A. D.; Longo, F. R.; Finarelli, J. D.; Goldmacher, J.; Assour, J.; Korsakoff, L. J. Org. Chem. 1967, 32, 476. doi:10.1021/jo01288a053
•  Lindsey, J. S.; Hsu, I. C.; Schreiman, I. C. Tetrahedron Lett.1986, 27, 4969. doi:10.1016/S0040-4039(00)85109-6
•  Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C. J. Org. Chem. 1987, 52, 827. DOI: 10.1021/jo00381a022
•  Laha, J. K.; Dhanalekshmi, S.; Taniguchi, M.; Ambroise, A.; Lindsey, J. S. Org. Proc. Res. Dev. 2003, 7, 799. DOI: 10.1021/op034083q

• Reaction Mechanism

Getting a high yield is usually difficult due to the formation of side products such as pyrrole oligomers.

• Examples

• Experimental Procedure

• Experimental Tips

• References

• Related Reactions

• Related Books

• External Links

Porphyrin – Wikipedia

condensation of aldehydes and pyrroles, synthesis of porphyrins