Expanded scope of synthetic bacteriochlorins via improved acid catalysis conditions and diverse dihydrodipyrrin-acetals

M Krayer, M Ptaszek, HJ Kim, KR Meneely…

Index: Krayer, Michael; Ptaszek, Marcin; Kim, Han-Je; Meneely, Kelly R.; Fan, Dazhong; Secor, Kristen; Lindsey, Jonathan S. Journal of Organic Chemistry, 2010 , vol. 75, # 4 p. 1016 - 1039

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Citation Number: 87

Abstract

Bacteriochlorins are attractive candidates for a wide variety of photochemical studies owing to their strong absorption in the near-infrared spectral region. The prior acid-catalysis conditions [BF3· O (Et) 2 in CH3CN at room temperature] for self-condensation of a dihydrodipyrrin-acetal (bearing a geminal dimethyl group in the pyrroline ring) typically afforded a mixture of three macrocycles: the expected 5-methoxybacteriochlorin (MeOBC- ...