Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal

• Main Authors: Philipp Honegger, Michael Widhalm
• Format: Article
• Language: English
• Published: MDPI AG 2019-11-01
• Series: Molbank
• Subjects: ferrocene; manganese dioxide; oxidation; planar chirality; diaza macrocycle; c–n bond formation
• Online Access: https://www.mdpi.com/1422-8599/2019/4/M1090
• ISSN: 1422-8599

In the course of an ongoing synthetic project, we observed an unprecedented reactivity of <i>N</i>-methyl groups in bis(<i>N</i>,<i>N</i>-dimethylaminoethylferrocenyl)phenylphosphinesulfide upon treatment with manganese dioxide (MnO₂). The intramolecular course of this reaction resulted in the formation of an unexpected homochiral diaza macrocycle. The target structure was accessible in two steps from known <i>N</i>,<i>N</i>-dimethylaminoethylferrocene.