Facile synthesis and purification of 1-acyldipyrromethanes

ORGN 601

Muthukumaran Kannan, Marcin Ptaszek, and Jonathan S. Lindsey. Department of Chemistry, North Carolina State University, Raleigh, NC 27695-8204
1-Acyldipyrromethanes (1) are important precursors in the synthesis of trans-A2B2, trans-AB2C, cis-A2B2, cis-AB2C, and ABCD porphyrins. 1-Acyldipyrromethanes streak upon chromatography and give amorphous powders upon attempted crystallization, thereby requiring lengthy chromatography for purification. We have developed a refined synthesis that sidesteps such handling problems and affords multigram quantities of 1-acyldipyrromethanes in a simple manner.