Sodium Hypochlorite

Galvin, Jennifer M.; Jacobsen, Eric N.; Palucki, Michael; Frederick, Michael O.

doi:10.1002/047084289x.rs084.pub3

Cited by 10 publications

(8 citation statements)

References 109 publications

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“…[12] While this approach dictates that the functionality present on the amine coupling partner is stable to NaOCl, this is am ilder oxidant with better functional group compatibility [13] than reagents typically used to generate Nhalo intermediates for HLF-type reactions (e.g.,i ns itu generated AcOI). [12] While this approach dictates that the functionality present on the amine coupling partner is stable to NaOCl, this is am ilder oxidant with better functional group compatibility [13] than reagents typically used to generate Nhalo intermediates for HLF-type reactions (e.g.,i ns itu generated AcOI).…”

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confidence: 99%

“…Thef unctionalized amine coupling partners in these studies were easily accessed from primary amines by ar eaction with dilute NaOCl followed by addition of adithiocarbamate salt. [12] While this approach dictates that the functionality present on the amine coupling partner is stable to NaOCl, this is am ilder oxidant with better functional group compatibility [13] than reagents typically used to generate Nhalo intermediates for HLF-type reactions (e.g.,i ns itu generated AcOI). [2] Standard amide couplings of the thiocarbamylsulfenamides with carboxylic acids then enabled ac onvergent synthesis of the N-dithiocarbamate substrates under mild conditions.…”

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confidence: 99%

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A General Approach to Site‐Specific, Intramolecular C−H Functionalization Using Dithiocarbamates

Alexanian

2018

Angewandte Chemie

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Intramolecular hydrogen atom transfer is an established approach for the site-specific functionalization of unactivated, aliphatic CÀHb onds.T ransformations using this strategy typically require unstable intermediates formed using strong oxidants and have mainly targeted CÀHh alogenations or intramolecular aminations.Herein, we report asite-specific C À Hfunctionalization that significantly increases the synthetic scope and convergency of reactions proceeding via intramolecular hydrogen atom transfer.S table,i solable N-dithiocarbamates are used as precursors to amidyl radicals formed via either light or radical initiation to efficiently deliver highly versatile alkyl dithiocarbamates across aw ide range of complex structures.

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confidence: 99%

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confidence: 99%

A General Approach to Site‐Specific, Intramolecular C−H Functionalization Using Dithiocarbamates

Alexanian

2018

Angewandte Chemie

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“…Hypochlorite exists in solution as a mixture of hypochlorite anion (ClO − ), hypochlorous acid (HOCl) and free chlorine (Cl 2 ) in pH-dependent amounts [91]. At physiological pH, ClO − and HOCl are the predominant molecules.…”

Section: Discussionmentioning

confidence: 99%

“…Hypochlorite oxidizes primary and secondary alcohols, and phenols. The first step of the above reactions is chlorination followed by hydrolysis/HCl elimination [91,92]. It is important to note that SDG contains all the reaction sites stated above (except amino groups), making the SDG molecule a potent hypochlorite scavenger.…”

Section: Discussionmentioning

confidence: 99%

Gamma-irradiation produces active chlorine species (ACS) in physiological solutions: Secoisolariciresinol diglucoside (SDG) scavenges ACS - A novel mechanism of DNA radioprotection

Mishra

Popov

Pietrofesa

et al. 2016

Biochimica et Biophysica Acta (BBA) - General Subjects

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Background Secoisolariciresinol diglucoside (SDG), the main lignan in whole grain flaxseed, is a potent antioxidant and free radical scavenger with known radioprotective properties. However, the exact mechanism of SDG radioprotection is not well understood. The current study identified a novel mechanism of DNA radioprotection by SDG in physiological solutions by scavenging active chlorine species (ACS) and reducing chlorinated nucleobases. Methods The ACS scavenging activity of SDG was determined using two highly specific fluoroprobes: hypochlorite-specific 3′-(p-aminophenyl) fluorescein (APF) and hydroxyl radical-sensitive 3′-(p-hydroxyphenyl) fluorescein (HPF). Dopamine, an SDG structural analog, was used for proton 1H NMR studies to trap primary ACS radicals. Taurine N-chlorination was determined to demonstrate radiation-induced generation of hypochlorite, a secondary ACS. DNA protection was assessed by determining the extent of DNA fragmentation and plasmid DNA relaxation following exposure to ClO− and radiation. Purine base chlorination by ClO− and γ-radiation was determined by using 2-aminopurine (2-AP), a fluorescent analog of 6-aminopurine. Results: Chloride anions (Cl−) consumed >90% of hydroxyl radicals in physiological solutions produced by γ-radiation resulting in ACS formation, which was detected by 1H NMR. Importantly, SDG scavenged hypochlorite- and γ-radiation-induced ACS. In addition, SDG blunted ACS-induced fragmentation of calf thymus DNA and plasmid DNA relaxation. SDG treatment before or after ACS exposure decreased the ClO− or γ-radiation-induced chlorination of 2-AP. Exposure to γ-radiation resulted in increased taurine chlorination, indicative of ClO− generation. NMR studies revealed formation of primary ACS radicals (chlorine atoms (Cl•) and dichloro radical anions (Cl2−•)), which were trapped by SDG and its structural analog dopamine. Conclusion We demonstrate that γ-radiation induces the generation of ACS in physiological solutions. SDG treatment scavenged ACS and prevented ACS-induced DNA damage and chlorination of 2-aminopurine. This study identified a novel and unique mechanism of SDG radioprotection, through ACS scavenging, and supports the potential usefulness of SDG as a radioprotector and mitigator for radiation exposure as part of cancer therapy or accidental exposure.

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“…Sodium hypochlorite (NaOCl) is an ideal oxidant in organic synthesis, 4 because it produces only non-toxic sodium chloride (NaCl) as a by-product following oxidation, and commercial aqueous NaOCl is non-explosive and inexpensive. Recently, we found that stable, crystalline sodium hypochlorite pentahydrate (NaOCl•5H 2 O), 5 which is now commercially available from several companies, is a very useful oxidant for the nitroxy radical-catalyzed oxidation of alcohols, 5b,5c as well as the oxidation of organosulfur compounds.…”

Section: Methodsmentioning

confidence: 99%

A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite

Kitagawa¹,

Mori²,

Odagiri³

et al. 2019

SynOpen

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N-Sulfonyloxaziridines (Davis’ oxaziridines) can be synthesized by reacting the corresponding N-sulfonylimines with aqueous sodium hypochlorite in acetonitrile without any catalyst. The pH of the aqueous sodium hypochlorite is crucial to obtain the product in high yield. Optimized conditions are presented that allow synthetically useful Davis’ oxaziridines to be easily obtained in up to 90% yields from the corresponding imines by using inexpensive, stable, environmentally friendly sodium hypochlorite pentahydrate crystals as the oxidant, with high reproducibility.

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Sodium Hypochlorite

Cited by 10 publications

References 109 publications

A General Approach to Site‐Specific, Intramolecular C−H Functionalization Using Dithiocarbamates

A General Approach to Site‐Specific, Intramolecular C−H Functionalization Using Dithiocarbamates

Gamma-irradiation produces active chlorine species (ACS) in physiological solutions: Secoisolariciresinol diglucoside (SDG) scavenges ACS - A novel mechanism of DNA radioprotection

A Concise, Catalyst-Free Synthesis of Davis’ Oxaziridines using Sodium Hypochlorite

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