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Paper | Special issue | Vol 90, No. 1, 2015, pp.238-251
Published online, 27th May, 2014
DOI: 10.3987/COM-14-S(K)10
Unusually Efficient Deformylative Synthesis of 1,2,8,9-Tetrasubstituted Dipyrrins from 4,5-Disubstituted Pyrrole-2-carbaldehydes

Mitsunori Oda,* Yurie Fujiwara, Yoshimitsu Kumai, Akira Ohta, and Ryuta Miyatake

*Department of Chemistry, Faculty of Science, Shinshu University, Asahi 3-1-1, Matsumoto, Nagano 390-8621, Japan


Upon heating in a mixture of hydrobromic acid and acetic acid, 4-arylmethyl-5-(4-methoxyphenyl)pyrrole-2-carbaldehydes (9ac) react to give 2,8-bis(arylmethyl)-1,9-bis(4-methoxyphenyl)dipyrrins (10ac) in high yields, demonstrating the first example of an unusually efficient deformylative transformation of pyrrole-2-carbaldehyde to dipyrrin. Dipyrrins 10 show a clear color change from red to blue, when exposed to Brønsted acid. Structure of 10a·H+ was determined by X-ray crystallographic analysis. The absorption change of 10a in the presence of a metal ion was also studied.