Investigation of the rearrangement in alkyl-bridged bis(carbamoyldiaziridine) derivatives
The thermal treatment of alkyl-bridged bis(carbamoyldiaziridine) derivatives in toluene at 100 °C led to the formation of new saturated five- and six-membered 1,3-diaza-heterocyclic compounds from ethylene- or propylene-bridged bis(carbamoyldiaziridine) derviatives, respectively. Detailed experiment...
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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
19 July 2012
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| In: |
European journal of organic chemistry
Year: 2012, Issue: 25, Pages: 4733-4739 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201200518 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/ejoc.201200518 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201200518 
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| Author Notes: | Matthias Kamuf, Frank Rominger, Oliver Trapp |
| Summary: | The thermal treatment of alkyl-bridged bis(carbamoyldiaziridine) derivatives in toluene at 100 °C led to the formation of new saturated five- and six-membered 1,3-diaza-heterocyclic compounds from ethylene- or propylene-bridged bis(carbamoyldiaziridine) derviatives, respectively. Detailed experimental investigations of this reaction revealed an unprecedented intramolecular eliminative rearrangement, involving the two adjacent diaziridine moieties. The loss of a three-carbon fragment by elimination of acetone during the reaction was confirmed by GC-MS measurements. The products of the rearrangement were fully characterized, and their structures were confirmed by X-ray crystal structure analysis. Furthermore, a reaction mechanism of the eliminative rearrangement was proposed, and the reaction pathway was corroborated by DFT calculations of gas-phase model structures at the B3LYP/6-31G** level. |
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| Item Description: | Gesehen am 30.05.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.201200518 |