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Synthesis of 1,5-diisopropyl substituted 6-oxoverdazyls
Organic & Biomolecular Chemistry (2005)
  • Emily C Paré, University of Detroit Mercy
  • David J R Brook, San Jose State University
  • Aaron Brieger, University of Detroit Mercy
  • Mick Badik, University of Detroit Mercy
  • Marie Schinke, University of Detroit Mercy
1,5-Diisopropyl-6-oxo-verdazyl free radicals were synthesized via the condensation of BOC protected isopropyl hydrazine with phosgene, deprotection with aqueous HCl, condensation with aldehydes to form tetrazanes and finally oxidation to give the free radicals. The introduction of isopropyl groups results in free radicals that show greater solubility in a variety of solvents and are more stable than their methyl substituted counterparts. ESR shows reduced hyperfine coupling to the isopropyl methine hydrogens consistent with this hydrogen being in the plane of the verdazyl ring.
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Emily C Paré, David J R Brook, Aaron Brieger, Mick Badik, et al.. "Synthesis of 1,5-diisopropyl substituted 6-oxoverdazyls" Organic & Biomolecular Chemistry Vol. 3 (2005)
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