Synthesis of Pyrrolidine-Fused [34]- and [36]Octaphyrins via 1,3-Dipolar Cycloaddition

The utility of expanded porphyrins as a dipolarophile in cycloaddition reactions has been investigated. The 1,3-dipolar cycloaddition of meso-octakis(pentafluorophenyl)[36]octaphyrin(1.1.1.1.1.1.1.1) with an azomethine ylide provides mono- and bis-pyrrolidine-fused octaphyrins regio-
and stereoselectively. Treatment of the cycloadduct with MnO2 afforded [34]octaphyrin quantitatively.

本研究考察了扩展卟啉（expanded porphyrins）作为亲偶极体（dipolarophile）在环加成反应中的应用潜力。中位-八(五氟苯基)[36]八卟啉(1.1.1.1.1.1.1.1)与甲亚胺叶立德（azomethine ylide）发生1,3-偶极环加成反应，区域和立体选择性地生成单吡咯烷稠合与双吡咯烷稠合八卟啉。将该环加合物经二氧化锰（MnO2）处理后，可定量得到[34]八卟啉。