Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal
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 (MnO<sub>2</sub>). The i...
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MDPI AG
2019-11-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2019/4/M1090 |
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doaj-15e3f0b9ec394a3688412a76c51439a02020-11-25T00:51:39ZengMDPI AGMolbank1422-85992019-11-0120194M109010.3390/M1090M1090Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminalPhilipp Honegger0Michael Widhalm1Institute of Computational Biological Chemistry, University of Vienna, Währinger Straße 17, Vienna 1090, AustriaInstitute of Chemical Catalysis, University of Vienna, Währinger Straße 38, Vienna 1090, AustriaIn 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 (MnO<sub>2</sub>). 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.https://www.mdpi.com/1422-8599/2019/4/M1090ferrocenemanganese dioxideoxidationplanar chiralitydiaza macrocyclec–n bond formation |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Philipp Honegger Michael Widhalm |
| spellingShingle |
Philipp Honegger Michael Widhalm Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal Molbank ferrocene manganese dioxide oxidation planar chirality diaza macrocycle c–n bond formation |
| author_facet |
Philipp Honegger Michael Widhalm |
| author_sort |
Philipp Honegger |
| title |
Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal |
| title_short |
Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal |
| title_full |
Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal |
| title_fullStr |
Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal |
| title_full_unstemmed |
Formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>S</i>)-2-[(1<i>R</i>)-1-(methylamino)-ethyl]]ferrocene-aminal |
| title_sort |
formaldehyde-1,1″-(phenylphosphinidenesulfide)bis[(2<i>s</i>)-2-[(1<i>r</i>)-1-(methylamino)-ethyl]]ferrocene-aminal |
| publisher |
MDPI AG |
| series |
Molbank |
| issn |
1422-8599 |
| publishDate |
2019-11-01 |
| description |
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 (MnO<sub>2</sub>). 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. |
| topic |
ferrocene manganese dioxide oxidation planar chirality diaza macrocycle c–n bond formation |
| url |
https://www.mdpi.com/1422-8599/2019/4/M1090 |
| work_keys_str_mv |
AT philipphonegger formaldehyde11phenylphosphinidenesulfidebis2isi21iri1methylaminoethylferroceneaminal AT michaelwidhalm formaldehyde11phenylphosphinidenesulfidebis2isi21iri1methylaminoethylferroceneaminal |
| _version_ |
1725244600733401088 |