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N,N′‐Ethylene‐Bridged Bis‐2‐Aryl‐Pyrrolinium Cations to E‐Diaminoalkenes: Non‐Identical Stepwise Reversible Double‐Redox Coupled Bond Activation Reactions
- Abstract This work presents a stepwise reversible two‐electron transfer induced hydrogen shift leading to the conversion of a bis‐pyrrolinium cation to an E‐diaminoalkene and vice versa. Remarkably, the forward and the reverse reaction, which are both reversible, follow two completely different reaction pathways. Establishing such unprecedented property in this type of processes was possible by developing a novel synthetic route towards the starting dication. All intermediates involved in both the forward and the backward reactions were comprehensively characterized by a combination of spectroscopic, crystallographic, electrochemical, spectroelectrochemical, and theoretical methods. The presented synthetic route opens up new possibilities for the generation of multi‐pyrrolinium cation scaffold‐based organic redox systems, which constitute decidedly sought‐after molecules in contemporary chemistry.
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| Author: | Mithilesh Kumar Nayak, Jessica Stubbe, Nicolás I. Neuman, Ramakirushnan Suriya Narayanan, Sandipan Maji, Carola SchulzkeORCiD, Vadapalli Chandrasekhar, Biprajit Sarkar, Anukul Jana |
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| URN: | urn:nbn:de:gbv:9-opus-40832 |
| DOI: | https://doi.org/10.1002/chem.202000255 |
| Parent Title (English): | Chemistry – A European Journal |
| Publisher: | Wiley |
| Place of publication: | Hoboken, New Jersey |
| Document Type: | Article |
| Language: | English |
| Date of first Publication: | 2020/04/01 |
| Release Date: | 2020/12/08 |
| Tag: | carbocations; electrochemistry; non-identical reversible reaction; radical reactions; redox chemistry |
| GND Keyword: | - |
| Volume: | 26 |
| Issue: | 19 |
| First Page: | 4425 |
| Last Page: | 4431 |
| Faculties: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie |
| Licence (German): |  Creative Commons - Namensnennung |