Aryl nitroporphycenes and derivatives: first regioselective synthesis of dinitroporphycenes

Autor:	David Sánchez-García, Gonzalo Anguera, Maria C. Llinàs, Xavier Batllori
Rok vydání:	2011
Předmět:	Acetic acid chemistry.chemical_compound Chemistry Yield (chemistry) Aryl Nitration Organic chemistry Fractional crystallization (chemistry) Regioselectivity Aromaticity General Chemistry Cis–trans isomerism
Zdroj:	Journal of Porphyrins and Phthalocyanines. 15:865-870
ISSN:	1099-1409 1088-4246
Popis:	The nitration reaction of 2,7,12,17-tetraphenylporphycene has been studied. The use of AgNO3 and a mixture of acetic acid and 1,2-dichloroethane as a mild nitrating system provides an optimized preparation of 9-nitro-2,7,12,17-tetraphenylporphycene and a regioselective synthesis of 9,20-dinitro-2,7,12,17-tetraphenylporphycene. While 25 min of reaction are needed to obtain the mononitrated compound, 4 h are necessary to yield a mixture of 9,20-dinitro and 9,19-dinitro 2,7,12,17- tetraphenylporphycene in a proportion of 3 to 1. From this mixture, the geometric isomers can be isolated by fractional crystallization. 9-Nitro-2,7,12,17-tetraphenylporphycene can be reduced to the corresponding amino derivative, which is the starting material to obtain 9-(glutaric methylesteramide)- 2,7,12,17-tetraphenylporphycene, a versatile derivative useful for conjugation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9ea71ab324717de6c19061ca5fc9e82d https://doi.org/10.1142/s1088424611003744 Zobrazit plný text záznamu