ORGN 371 |
Refined synthesis of 1,9-diacyldipyrromethane
| Shun-ichi Tamaru, Justin Youngblood, Kannan Muthukumaran, Lianhe Yu, and Jonathan S. Lindsey. Department of Chemistry, North Carolina State University, Raleigh, NC 27696-8204 |
Meso-substituted porphyrins bearing specific patterns of functional groups are valuable components in the synthesis of porphyrin-based biomimetic systems and molecular materials. Dipyrromethanes bearing acyl groups at the 1- and 9-positions are key precursors to such porphyrins. Dipyrromethanes bearing identical groups at the 1- and 9-positions enable synthesis of trans-AB2C-porphyrins, while those with different groups enable the synthesis of porphyrins bearing four different substituents (ABCD-porphyrins). Two distinct methods for diacylation with identical acyl species include (1) treatment with EtMgBr followed by an acid chloride, or (2) alkylation with a 2-aryl-1,3-benzoxathiolium tetrafluoroborate followed by oxidative hydrolysis. Both methods require chromatography to separate the diacyl and monoacyl dipyrromethanes. We have developed improved acylation chemistry and separation methodology that facilitate synthesis and isolation of 1,9-diacyldipyrromethanes. |
| |
|
Physical Organic, Materials, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Tuesday, September 9, 2003 Hilton New York -- Americas Hall 1, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
|