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Related Concept Videos

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
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Phase I biotransformation, or functionalization, is a crucial chemical process that converts drugs and other xenobiotics into more water-soluble forms, facilitating expulsion from the body. It involves oxidative, reductive, and hydrolytic reactions that add or unveil polar functional groups on lipophilic substrates. Key players in phase I reactions are the mixed-function oxidases. Situated in liver cell microsomes, these enzymes predominantly carry out drug metabolism. They require molecular...
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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Iodoarene-catalyzed oxidative transformations using molecular oxygen.

K Miyamoto1, J Yamashita, S Narita

  • 1Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. kmiya@mol.f.u.-tokyo.ac.jp uchiyama@mol.f.u-tokyo.ac.jp.

Chemical Communications (Cambridge, England)
|August 18, 2017
PubMed
Summary

Molecular oxygen efficiently oxidizes diols and amides using a pentamethyliodobenzene catalyst. This method utilizes isobutyraldehyde and nitriles to facilitate an iodine catalytic cycle with in situ-generated peracid as the oxidant.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Oxidation Reactions

Background:

  • Molecular oxygen is a sustainable and economical oxidant.
  • Efficient catalytic systems are crucial for green chemistry.
  • 1,2-diol scission and Hofmann rearrangement are important synthetic transformations.

Purpose of the Study:

  • To develop a catalytic system using molecular oxygen for glycol scission and Hofmann rearrangement.
  • To investigate the role of pentamethyliodobenzene in a catalytic iodine cycle.
  • To explore the use of isobutyraldehyde and Lewis basic nitriles in oxidation reactions.

Main Methods:

  • Catalytic oxidation of 1,2-diols and primary amides.
  • Utilizing pentamethyliodobenzene as a catalyst.
  • Employing molecular oxygen as the terminal oxidant in the presence of isobutyraldehyde and Lewis basic nitriles.

Main Results:

  • Pentamethyliodobenzene effectively catalyzes glycol scission and Hofmann rearrangement under O2.
  • An iodine(I)/(III) catalytic cycle was established.
  • In situ-generated peracid was identified as the terminal oxidant, facilitated by isobutyraldehyde and nitriles.

Conclusions:

  • This study presents a novel and efficient aerobic oxidation method for key organic transformations.
  • The developed catalytic system offers a greener alternative to traditional oxidation methods.
  • The mechanistic insights into the iodine catalytic cycle provide a foundation for further catalyst development.