New, Milder Hypervalent Iodine Oxidizing Agent: Using μ-Oxodi(phenyliodanyl) Diacetate, a (Diacetoxyiodo)benzene Derivative, in the Synthesis of Quinones

Hao Che Peng, Jessica Bryan, William Henson, Viktor V. Zhdankin, Kushal Gandhi, Samuel David

Research output: Contribution to journalArticle

Abstract

The synthesis of substituted 1,4-benzoquinones, a biologically important class of compounds, was developed using μ-oxodi(phenyliodanyl) diacetate, a (diacetoxyiodo)benzene-based oxidizing reagent, in order to introduce second-year undergraduate organic laboratory students in their second semester or advanced organic students to increasingly popular and environmentally friendly hypervalent iodine chemistry. This experiment develops on concepts found in the undergraduate organic chemistry curriculum; conveniently fits into approximately two 3 h lab modules; and utilizes regularly found equipment and inexpensive, commercially available chemicals.

Original languageEnglish (US)
Pages (from-to)2622-2627
Number of pages6
JournalJournal of Chemical Education
Volume96
Issue number11
DOIs
StatePublished - Nov 12 2019
Externally publishedYes

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Benzene Derivatives
Quinones
Oxidants
Iodine
chemistry
Benzoquinones
Students
Benzene
Curricula
semester
student
curriculum
experiment
Experiments

Keywords

  • Green Chemistry
  • Hands-On Learning/Manipulatives
  • Laboratory Instruction
  • Medicinal Chemistry
  • Organic Chemistry
  • Oxidation/Reduction
  • Second-Year Undergraduate
  • Spectroscopy
  • Synthesis
  • Upper-Division Undergraduate

Cite this

New, Milder Hypervalent Iodine Oxidizing Agent : Using μ-Oxodi(phenyliodanyl) Diacetate, a (Diacetoxyiodo)benzene Derivative, in the Synthesis of Quinones. / Peng, Hao Che; Bryan, Jessica; Henson, William; Zhdankin, Viktor V.; Gandhi, Kushal; David, Samuel.

In: Journal of Chemical Education, Vol. 96, No. 11, 12.11.2019, p. 2622-2627.

Research output: Contribution to journalArticle

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