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

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 language	English
Pages (from-to)	2622-2627
Number of pages	6
Journal	Journal of Chemical Education
Volume	96
Issue number	11
DOIs	https://doi.org/10.1021/acs.jchemed.8b00636
Publication status	Published - 12 Nov 2019
Externally published	Yes

Keywords

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

ASJC Scopus subject areas

Chemistry(all)
Education

Access to Document

10.1021/acs.jchemed.8b00636

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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 journal › Article › peer-review

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

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.",

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

author = "Peng, {Hao Che} and Jessica Bryan and William Henson and Zhdankin, {Viktor V.} and Kushal Gandhi and Samuel David",

note = "Funding Information: This research was supported by a Robert A. Welch Foundation Chemistry Department Research Grant (AW-0013) and the Louis Stokes Association Minority Program, funded by National Science Foundation grant number HRD-1202008, UTPB sub award no. 226100841L. We are grateful to Milka Montes and Kyle Beran from the University of Texas Permian Basin for help with the manuscript. Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society and Division of Chemical Education, Inc. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.",

year = "2019",

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doi = "10.1021/acs.jchemed.8b00636",

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AU - Zhdankin, Viktor V.

AU - Gandhi, Kushal

AU - David, Samuel

N1 - Funding Information: This research was supported by a Robert A. Welch Foundation Chemistry Department Research Grant (AW-0013) and the Louis Stokes Association Minority Program, funded by National Science Foundation grant number HRD-1202008, UTPB sub award no. 226100841L. We are grateful to Milka Montes and Kyle Beran from the University of Texas Permian Basin for help with the manuscript. Publisher Copyright: Copyright © 2019 American Chemical Society and Division of Chemical Education, Inc. Copyright: Copyright 2019 Elsevier B.V., All rights reserved.

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