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Synfacts 2013; 9(1): 0039
DOI: 10.1055/s-0032-1317888
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Formation of an Unusual Four-Membered Nitrogen Ring

Contributor(s):
Timothy M. Swager
,
Markrete Krikorian
Camp D, * Campitelli M, Hanson GR, Jenkins ID. Griffith University, Nathan and University of Queensland, St. Lucia, Australia
Formation of an Unusual Four-Membered Nitrogen Ring (Tetrazetidine) Radical Cation.

J. Am. Chem. Soc. 2012;
134: 16188-16196
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Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

diquinone-based cavitands - molecular machines - resorcin[4]arenes

Significance

Above is one of three proposed mechanisms for the formation of the new radical cationic nitrogen four-membered ring 5. This tetrazetidine forms from allowing triphenylphosphine and diisopropyl azodicarboxylate to react. Previous studies had shown cursory evidence for the formation of a tetrazetidine by other methods, while this work offers more conclusive evidence in the form of EPR spectra and DFT calculations.


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Comment

The reaction was monitored by EPR spectroscopy, which showed the presence and disappearance of 3 followed by the formation of 5. Thus, the authors claim that the above mechanism is the most plausible. The DFT calculations show electron density on the methine or methylene protons (R = Et, i-Pr), which helps to rationalize hydrogen hyperfine coupling seen on the EPR spectra.


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