The balanced decarboxylation of aromatic polycarboxylic acids - a one-step synthesis of perylene-3,4-dicarboxylic acid anhydride

摘要

Preparation of perylene-3,4-dicarboxylic anhydrides of formula (I) in which R1, R2, R3, R4, R5, R6, R7, R8 are hydrogen, or one radical to eight radicals are a radical selected from the group consisting of an unsubstituted or substituted carbocyclic aromatic radical, an unsubstituted or substituted heterocyclic aromatic radical, halogen, unsubstituted or substituted C1-C18alkyl, -OR9, CN, -NR10R11, -COR12, -NR13COR12, -NR9COOR12, -NR9CONR10R11, -NHSO2R12, -SO2R12, -SOR12, -SO2OR12, -CONR10R11, -SO2NR10R11, -N=NR14, -OCOR12 and -OCONHR12, where each two adjacent radicals together can form a carbocyclic or heterocyclic ring; where R12 is C1-C18alkyl, C6-C10aryl or benzyl which is unsubstituted or substituted by halogen, C1-C4alkyl or C1-C4alkoxy or is a five- to seven-membered heterocyclic radical, R10 and R11 independently of one another are hydrogen, C1-C18alkyl, C3-C24cycloalkyl, C6-C10-aryl, each of which is unsubstituted or substituted by cyano or hydroxyl groups or 5- to 7-membered heteroaryl, or in which R10 and R11 together with at least one of the other radicals R1 to R8 form a 5- or 6-membered carbocyclic or heterocyclic ring; R9 is hydrogen, C1-C18alkyl, C3-C24cycloalkyl, C6-C10aryl or 5- to 7-membered heteroaryl, R13 is hydrogen, C1-C18alkyl, C3-C24cycloalkyl, C1-C4alkylaryl, each of which is unsubstituted or substituted by cyano, hydroxyl or C1-C4alkoxycarbonyl groups, C6-C10aryl which is unsubstituted or substituted by halogen, C1-C4alkyl or C1-C4alkoxy groups, or is a 5- to 7-membered heterocycle, and R14 is the radical of a coupling component or C6-C10aryl which is unsubstituted or substituted by halogen, C1-C4alkyl or C1-C4alkoxy groups by reacting perylene-3,4:9,10-tetracarboxylic anhydride of formula (II) in which R1 to R8 are defined as indicated above, with a sterically hindered amine as a base at elevated temperature, processes for the preparation of further perylene derivatives, perylene derivatives and their use.