Oxidative cleavage
Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations and reductions are different from ordinary redox reactions because many reactions carry the name but do not actually involve electron transfer in the electrochemical sense of the word.
Simple functional groups can be arranged in order of increasing oxidation state. The oxidation numbers are only an approximation:
- oxidation number -4 for alkanes,
- oxidation number -2 for alkenes, alcohols, alkyl halides, amines,
- oxidation number 0 for alkynes, ketones, aldehydes, geminal diols,
- oxidation number +2 for carboxylic acids, amides, chloroform and
- oxidation number +4 for carbon dioxide, tetrachloromethane.
When methane is oxidized to carbon dioxide its oxidation number changes from -4 to +4. Classical reductions include alkene reduction to alkanes and classical oxidations include oxidation of alcohols to aldehydes. In oxidations electrons are removed and the electron density of a molecule is reduced. In reductions electron density increases when electrons are added to the molecule. This terminology is always centered around the organic compound. For example, it is usual to refer to the reduction of a ketone by lithium aluminium hydride, but not to the oxidation of lithium aluminium hydride by a ketone. Many oxidations involve removal of hydrogen atoms from the organic molecule, and the reverse reduction adds hydrogens to an organic molecule.
Many reactions classified as reductions also appear in other classes. For instance conversion of the ketone to an alcohol by lithium aluminium hydride can be considered a reduction but the hydride is also a good nucleophile in nucleophilic substitution. Many redox reactions in organic chemistry have coupling reaction reaction mechanism involving free radical intermediates. True organic redox chemistry can be found in electrochemical organic synthesis or electrosynthesis. Examples of organic reactions that can take place in an electrochemical cell are the Kolbe electrolysis
In disproportionation reactions the reactant is both oxidised and reduced in the same chemical reaction forming 2 separate compounds.
Asymmetric catalytic reductions and asymmetric catalytic oxidations are important in asymmetric synthesis.

This is an excerpt from the article Oxidative cleavage from the Wikipedia free encyclopedia. A list of authors is available at Wikipedia.
The article Oxidative cleavage at en.wikipedia.org was accessed 40 times in the last 30 days. (as of: 11/06/2013)
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Introduction to Oxidative Cleavage Reactions — Master Organic ...
Nov 1, 2011 ... Here's a post on one of the most important reaction patterns in all of Org 1 – Oxidative cleavage.
www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/
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Oxidative Cleavage of Double Bonds - Chemwiki
Oct 1, 2013 ... Ozonolysis. In determining the structural formula of an alkene, it is often necessary to find the location of the double bond within a given carbon ...
chemwiki.ucdavis.edu/Organic_Chemistry/Hydrocarbons/Alkenes/Reactions_of_Alkenes/Stereoselectivity_in_Addition_Reactions_to_Double_Bonds/Oxidations/Oxidative_Cleavage_of_Double_Bonds
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Alkenes: Oxidation and Cleavage Reactions - CliffsNotes
Alkenes can easily be oxidized by potassium permanganate and other oxidizing agents. What products form depend on the reaction conditions. At cold ...
www.cliffsnotes.com/sciences/chemistry/organic-chemistry-i/reactions-of-alkenes/alkenes-oxidation-and-cleavage-reactions
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Oxidative Cleavage of Alkenes and Alkynes by Ozonolysis or ...
Oxidative cleavage of Alkenes and Alkynes by. Ozonolysis or Potassium Permanganate. In Chapter 10 of Fox and Whitesell (pp 520-524), there is a relatively ...
home.cc.umanitoba.ca/~hultin/chem2220/Support/oxidative_cleavage.pdf
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Oxidative Cleavage of Alkenes - The WikiPremed MCAT Course
Oxidative cleavage of Alkenes. In basic conditions, treatment of alkene with potassium permanganate forms a vicinal diol. Oxidative cleavage by permanganate ...
www.wikipremed.com/03_organicmechanisms.php?mch_code=030202_080
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Oxidative Cleavage of a double bond | Student Doctor Network
Apr 24, 2013 ... Why is cleavage of a double bond an oxidative process?
forums.studentdoctor.net/threads/oxidative-cleavage-of-a-double-bond.1000087/
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Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes
Ruthenium-Catalyzed Oxidative cleavage of Olefins to Aldehydes. Dan Yang* and Chi Zhang. *Department of Chemistry, The University of Hong Kong, ...
www.organic-chemistry.org/abstracts/literature/567.shtm
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Ch15: Oxidation cleavage of 1,2-diols
1,2- or vicinal diols are cleaved by periodic acid, HIO4, into two carbonyl compounds. The reaction is selective for 1,2-diols. The reaction occurs via the formation ...
www.chem.ucalgary.ca/courses/350/Carey5th/Ch15/ch15-4-7.html
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What is oxidative cleavage? - Yahoo Answers
Oxidative cleavage is the breaking of bonds involving a process that oxidizes the atoms that were formerly connected: After cleavage, each sulfur ...
answers.yahoo.com/question/index?qid=20111106030308AAawZbC
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Cleavage of 1,2-Diols - McGraw-Hill
Oxidative cleavage of Diols. Chapter ... Reaction type: Oxidation-reduction. Summary. 1,2- or vicinal diols are cleaved by periodic acid, HIO4, into two carbonyl ...
www.mhhe.com/physsci/chemistry/carey/student/olc/ch15oxidativecleavagediols.html
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Oxidative cleavage in science
Oxidative Cleavage of Double Bonds - Chemwiki
Oct 1, 2013 ... This Oxidative cleavage of a carbon-carbon single bond provides a two-step, ... UC Davis GeoWiki by University of California, Davis is licensed ...
Alkene Reactivity
Some oxidation reactions of alkenes give cyclic ethers in which both carbons of .... This Oxidative cleavage of a carbon-carbon single bond provides a two-step, ...
[PDF]Ruthenium-Catalyzed Oxidative Cleavage of Alkynes - American ...
Department of Chemistry, The University of Hong Kong,. Pokfulam Road, Hong ... and ultrasound2b can promote the Oxidative cleavage of alkynes by potassium ...
[PDF]279 Electrochemical Oxidative Cleavage of ... - Indiana University
Oxidative cleavage under varied environmental conditions, like extraterrestrial or deep sea ... group or by the Indiana University (IU) Mass Spectrometry Facility.
Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes
Ruthenium-Catalyzed Oxidative cleavage of Olefins to Aldehydes. Dan Yang* and Chi Zhang. *Department of Chemistry, The University of Hong Kong, ...
Metal-Free, NHPI Catalyzed Oxidative Cleavage of CC Double Bond ...
Metal-Free, NHPI Catalyzed Oxidative cleavage of C-C Double Bond Using ... * State Key Laboratory of Natural and Biomimetic Drugs, Peking University, School  ...
Specific Oxidative Cleavage of Carotenoids by VP14 of Maize
The plant growth regulator abscisic acid (ABA) is formed by the Oxidative cleavage of an epoxy-carotenoid. The synthesis of other apocarotenoids, such as  ...
Secologanin synthase which catalyzes the oxidative cleavage of ...
... Plants Garden, School of Pharmaceutical Sciences, Nagasaki University, Japan. Secologanin synthase, an enzyme catalyzing the Oxidative cleavage of the ...
Oxidative DNA Cleavage Mediated by Copper Complexes
... School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, ... Abstract In this review, the mechanism of the oxidative DNA cleavage ... In addition, the photo-induced DNA cleavage by copper complexes has also ...
Ch15: Oxidation cleavage of 1,2-diols - Chemistry - University of ...
1,2- or vicinal diols are cleaved by periodic acid, HIO4, into two carbonyl compounds. The reaction is selective for 1,2-diols. The reaction occurs via the formation ...
Books on the term Oxidative cleavage
Advanced Organic Chemistry: Part B: Reaction and Synthesis
Advanced Organic Chemistry: Part B: Reaction and Synthesis
Francis A. Carey, Richard J. Sundberg, 2007
1127), the glycol unit is susceptible to mild Oxidative cleavage. The most commonly used reagent for this Oxidative cleavage is the periodate ion.261 The fragmentation is believed to occur via a cyclic adduct of the glycol and the oxidant .
Oxidative cleavage of olefins mediated by osmium tetroxide and efforts toward elaboration of a pyrrolidine synthon...
Oxidative cleavage of olefins mediated by osmium tetroxide and efforts toward elaboration of a pyrrolidine synthon...
2011
Enjoy a wide range of dissertations and theses published from graduate schools and universities from around the world. Covering a wide range of academic topics, we are happy to increase overall global access to these works and make them available outside of traditional academic databases. These works are packaged and produced by BiblioLabs under li...
Oxidative Folding of Peptides and Proteins
Oxidative Folding of Peptides and Proteins
Luis Moroder, Johannes Buchner (Prof.), 2009
Subsequent cleavage of the StBu groups was achieved by tributylphosphine, thereby generating the dithiol-peptide for the first disulfide formation by exposure to air oxygen, followed by I2 oxidation to generate the second disulfide bond.
Oxidation
Oxidation
Barry M. Trost, Steven V. Ley, Ian Fleming, 1991
4-Cyclooctene, hydroperoxy- synthesis, 728 Cyclooctene, 1-phenyl- oxidation, 384 Cyclooctyne synthesis via ... via Oxidative cleavage of alkenes, 558 1 ,2- Cyclopentanediol oxidation sodium bismuthate, 704 Oxidative cleavage, 705, 708 ...
Non-enzymatic Site-specific Cleavage of Proteins for the ...
Non-enzymatic Site-specific Cleavage of Proteins for the ...
Nicolas J. Hauser, 2008
When the microwave is turned on with no voltage applied, the peak corresponding to D-cleavage is observed at m/z's 1181.8 (+1) and 591.4 (+2) and no peaks can be assigned to electrochemical Oxidative cleavage. Likewise, with no ...
Methods in Biological Oxidative Stress (Methods in Pharmacology and Toxicology)
Methods in Biological Oxidative Stress (Methods in Pharmacology and Toxicology)
2003
Free radicals and reactive oxidizing agents are now recognized as causes or contributing factors in inflammation and other disease states and have become a major focus of interest in pharmacology, toxicology, physiology, and biochemistry. In Methods in Biological Oxidative Stress, expert researchers detail their best experimental methods for detect...
The Porphyrin Handbook: Biochemistry and binding: activation ...
The Porphyrin Handbook: Biochemistry and binding: activation ...
Karl M. Kadish, Kevin M. Smith, Roger Guilard, 2000
The latter, which can be prepared by oxidative addition of superoxide to synthetic ferrous porphyrin complexes, deserves ... This section deals with oxidative by opposition to hydrolytic DNA cleavage.871 Bleomycin (BLM), is a naturally ...
Inflammation, Oxidative Stress, and Cancer: Dietary Approaches for Cancer Prevention
Inflammation, Oxidative Stress, and Cancer: Dietary Approaches for Cancer Prevention
2013
Increasing scientific evidence suggests that the majority of diseases including cancer are driven by oxidative stress and inflammation, attributed to environmental factors. These factors either drive genetic mutations or epigenetically modify expression of key regulatory genes. These changes can occur as early as gestational fetal development, and ...
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Blog posts on the term
Oxidative cleavage
Oxidative Cleavage of β-Lactam Ring of Cephalosporins with Chloramine-T in Alkaline Medium: A Kinetic, Mechanistic, and Reactivity Study
ISRN Physical Chemistry is a peer-reviewed, open access journal that publishes original research articles as well as review articles in all areas of physical chemistry.
www.hindawi.com/isrn/physical.chemistry/2013/738932/
Marine Drugs | Free Full-Text | Optimal Cleavage and Oxidative Folding of α-Conotoxin TxIB as a Therapeutic Candidate Peptide
Alpha6beta2 nicotinic acetylcholine receptors (nAChRs) are potential therapeutic targets for the treatment of several neuropsychiatric diseases, including addiction and Parkinson’s disease. Alpha-conotoxin (α-CTx) TxIB is a uniquely selective ligand, which blocks α6/α3β2β3 nAChRs only, but does not block the other subtypes. Therefore, α-CTx TxIB is a valuable therapeutic candidate peptide. Synthesizing enough α-CTx TxIB with high yield production is required for conducting wide-range testing of its potential medicinal applications. The current study optimized the cleavage of synthesized α-CTx TxIB resin-bounded peptide and folding of the cleaved linear peptide. Key parameters influencing cleavage and oxidative folding of α-CTx TxIB were examined, such as buffer, redox agents, pH, salt, co-solvent and temperature. Twelve conditions were used for cleavage optimization. Fifty-four kinds of one-step oxidative solution were used to assess their effects on each α-CTx TxIB isomers’ yield. The result indicated that co-solvent choices were particularly important. Completely oxidative folding of globular isomer was achieved when the NH4HCO3 or Tris-HCl folding buffer at 4 °C contained 40% of co-solvent DMSO, and GSH:GSSG (2:1) or GSH only with pH 8~8.7.
www.mdpi.com/1660-3397/11/9/3537
Introduction to Oxidative Cleavage Reactions — Master Organic Chemistry
Here’s a post on one of the most important reaction patterns in all of Org 1 – Oxidative cleavage
www.masterorganicchemistry.com/2011/11/01/introduction-to-oxidative-cleavage-reactions/
Regioselective Control in the Oxidative Cleavage of 4,6-O-Benzylidene Acetals of Glycopyranosides by Dimethyldioxirane - The Journal of Organic Chemistry (ACS Publications)
pubs.acs.org/doi/abs/10.1021/jo9026098
An Expedient Procedure for the Oxidative Cleavage of Olefinic Bonds with PhI(OAc)2, NMO, and Catalytic OsO4 - Organic Letters (ACS Publications)
pubs.acs.org/doi/abs/10.1021/ol100290a
San Diego: Klotho Spins Threads Linking Aging and AD Research | ALZFORUM
www.alzforum.org/news/conference-coverage/san-diego-klotho-spins-threads-linking-aging-and-ad-research
Organosynthetic & Organometallic Chemistry: Oxidative cleavage of α-hydroxyketones
Tetrahedron Letters 50 (2009) 5399–5402  " The Oxidative cleavage of vicinal diols, a-hydroxyketones, and related functionalities is a common synthetic procedure and various reagents are available to perform this reaction, such as sodium bismuthate,1 iodo triacetate,2 manganic pyrophosphate,3 KHSO5,4 calcium hypochlorite,5 basic hydrogen peroxide,6 methylrhenium trioxide,7 Bi/O2,8 sodium percarbonate,9 and vanadium-based HPA and dioxygen. 10 However, the most versatile reagents for this purpose are sodium metaperiodate,11 and lead tetraacetate.
tvv2008.blogspot.com/2010/11/oxidative-cleavage-of-hydroxyketones.html
Alkene Reactions: Ozonolysis — Master Organic Chemistry
Today’s post represents not so much a pattern in alkene reactions, so much as it does a very common reaction that bears mentioning along with the rest. What makes this reaction special is that it does not simply break the carbon-carbon π […]
www.masterorganicchemistry.com/2013/04/23/alkene-reactions-ozonolysis/
Is the Oxidative DNA Damage Level of Human Lymphocyte Correlated with the Antioxidant Capacity of Serum or the Base Excision Repair Activity of Lymphocyte?
Oxidative Medicine and Cellular Longevity is a unique peer-reviewed journal that publishes original research and review articles dealing with the cellular and molecular mechanisms of oxidative stress in the nervous system and related organ systems in relation to aging, immune function, vascular biology, metabolism, cellular survival and cellular longevity. Oxidative stress impacts almost all acute and chronic progressive disorders and on a cellular basis is intimately linked to aging, cardiovascular disease, cancer, immune function, metabolism and neurodegeneration. The journal fills a significant void in today’s scientific literature and serves as an international forum for the scientific community worldwide to translate pioneering “bench to bedside” research into clinical strategies.
www.hindawi.com/journals/omcl/2013/237583/
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