title: Electrophilic iodination: a gateway to high iodine compounds and energetic materials.
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.
authors: Department of Chemistry, University of Idaho, Moscow, ID 83844-2343, USA. jshreeve@uidaho.edu.
authors: Deepak
authors: D
authors: Chand
authors: Chunlin
authors: C
authors: He
authors: Lauren A
authors: LA
authors: Mitchell
authors: Damon A
authors: DA
authors: Parrish
authors: Jean'ne M
authors: JM
authors: Shreeve