Protecting Triazabutadienes To Afford Acid Resistance

Lindsay E. Guzman, Flora W. Kimani, John C. Jewett

Research output: Contribution to journalArticlepeer-review

8 Scopus citations


Recent work on triazabutadienes has shown that they have the ability to release aryl diazonium ions under exceptionally mild acidic conditions. There are instances that require that this release be prevented or minimized. Accordingly, a base-labile protection strategy for the triazabutadiene is presented. It affords enhanced synthetic and practical utility of the triazabutadiene. The effects of steric and electronic factors in the rate of removal are discussed, and the triazabutadiene protection is shown to be compatible with the traditional acid-labile protection strategy used in solid phase peptide synthesis.

Original languageEnglish (US)
Pages (from-to)2220-2222
Number of pages3
Issue number23
StatePublished - Dec 2 2016


  • acid/base chemistry
  • aryl diazonium ion
  • hydrolysis
  • protecting groups
  • solid-phase synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Organic Chemistry


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