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Issue 35, 2016
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Electrophilic iodination: a gateway to high iodine compounds and energetic materials

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Abstract

A large number of iodine atoms can be introduced into a single molecule in a one-pot reaction using trifluoroperacetic acid-mediated electrophilic iodination methodology. The scope of this reaction was investigated extensively using several pyrazole substrates which resulted in nine polyiodo pyrazole compounds with iodine content as high as 80%. This synthetic methodology was also utilized successfully for iodination of benzimidazoles. Tetraiodobenzimidazole was nitrated with 100% nitric acid to give a high yield of 4,5,6,7-tetranitro-1H-benzimidazol-2(3H)-one (14). All of these materials were fully characterized and compounds 5, 9, 10 and 14 were confirmed further with single crystal X-ray analysis. High density, positive oxygen balance, and very good impact sensitivity values characterize 14. For the first time, two 1,2,5-oxadiazole-N-oxide rings were introduced into a benzimidazole ring (11) which remarkably improves the stability of oxadiazole-N-oxide compounds.

Graphical abstract: Electrophilic iodination: a gateway to high iodine compounds and energetic materials

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Publication details

The article was received on 18 Jun 2016, accepted on 07 Aug 2016 and first published on 09 Aug 2016


Article type: Paper
DOI: 10.1039/C6DT02438F
Citation: Dalton Trans., 2016,45, 13827-13833
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    Electrophilic iodination: a gateway to high iodine compounds and energetic materials

    D. Chand, C. He, L. A. Mitchell, D. A. Parrish and J. M. Shreeve, Dalton Trans., 2016, 45, 13827
    DOI: 10.1039/C6DT02438F

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