Synthesis of porphyrins bearing one or two meso substituents

ORGN 649

Masahiko Taniguchi,, Dazhong Fan, and Jonathan S. Lindsey, Department of Chemistry, North Carolina State University, Box 8204, Raleigh, NC 27695-8204

5,15-Disubstituted porphyrins are valuable compounds in bioorganic and materials chemistry.  A new rational synthesis has been developed that employs condensation of a dipyrromethane + a 1,9-disubstituted dipyrromethane derivative affording the zinc porphyrin.  Several C1 synthons have been investigated at the 1,9-positions of the dipyrromethane.  The synthesis is compatible with diverse meso-substituents (e.g., H, alkyl, aryl, ester, acetal) and enables rapid synthesis of trans-AB-, A2-, and A-porphyrins without detectable scrambling.  The synthesis of >50 zinc porphyrins has been surveyed.



Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005