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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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Hauptverfasser: Kamuf, Matthias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Trapp, Oliver (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 19 July 2012
In: European journal of organic chemistry
Year: 2012, Heft: 25, Pages: 4733-4739
ISSN:1099-0690
DOI:10.1002/ejoc.201200518
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/ejoc.201200518
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201200518
Volltext
Verfasserangaben:Matthias Kamuf, Frank Rominger, Oliver Trapp

MARC

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520 |a 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. 
650 4 |a Density functional calculations 
650 4 |a Nitrogen heterocycles 
650 4 |a Reaction mechanisms 
650 4 |a Sigmatropic rearrangement 
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