1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane as new oxidant for chemoselective and catalyst free oxidation of sulfides to sulfoxides and sulfones

Khosravi, Kaveh; Naserifar, Shirin; Mahmoudi, Boshra; Khalaji, Kobra

doi:10.1080/10426507.2016.1237951

Cited by 5 publications

References 42 publications

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1,2‐Diphenyl‐1,1,2,2‐tetrahydroperoxyethane

Kaveh

2024

Encyclopedia of Reagents for Organic Synthesis

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image [1877235‐95‐4] C 14 H 14 O 8 (MW 310.26) InChI = 1S/C14H14O8/c15‐19‐13(20‐16,11‐7‐3‐1‐4‐8‐11)14(21‐17,22‐18)12‐9‐5‐2‐6‐10‐12/h1‐10,15‐18H InChIKey = YUKVUSPUUYUWCD‐UHFFFAOYSA‐N (a powerful solid peroxide type oxidant, an alternative for aqueous hydrogen peroxide, and other similar hydroperoxides) IUPAC Name: 1,1,2,2‐tetrahydroperoxy‐1,2‐diphenylethane (THPDPE). Physical Data: white solid, Mp: 97–100 °C. Analysis of Reagent Purity: Ft‐IR, 1 H‐NMR, 13 C‐NMR, CHN (elemental analysis). Solubility: soluble in ethanol, methanol, acetic acid, and some similar organic solvents, such as water (nearly). Preparative Method: Caution: in all the reported articles, it is emphasized that this reagent is safe. However, it is important to note that all peroxides possess the potential for explosiveness and therefore should be handled with utmost caution. All reactions involving this reagent should be conducted behind a safety shield within a fume hood. Additionally, it is advisable to steer clear of using transition metal salts or direct heating in conjunction with this reagent. To begin the reaction, SbCl 3 ( 23 mg, 0.1 mmol) was added to a stirred solution of benzil (210 mg, 1 mmol) in CH 3 CN (5 mL), which was then stirred for 5 min at room temperature. Next, aqueous 30% H 2 O 2 (5 mmol) was added, and the resulting reaction mixture was allowed to stir for 24 h at room temperature. Upon completion, water (5 mL) was added. The product was then extracted using ethyl acetate. The organic layer was evaporated under reduced pressure. This process yielded the pure product in a 97% yield (300 mg). 1

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1,2‐Diphenyl‐1,1,2,2‐tetrahydroperoxyethane

Kaveh

2024

Encyclopedia of Reagents for Organic Synthesis

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Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant

Khosravi

Naserifar

Mahmoudi

2017

Journal of the Chinese Chemical Society

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Urea‐2,2‐dihydroperoxypropane as a Novel and High Oxygen Content Alternative to Dihydroperoxypropane in Several Oxidation Reactions

Khosravi

Naserifar

2019

ChemistrySelect

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Urea‐2,2‐dihydroperoxypropane (UDHPP)‐ a white crystalline solid oxidant which is formed when urea is recrystallized from dihydroperoxypropane‐ was applied as the terminal oxidant in several oxidative procedures namely epoxidation of α, β‐unsaturated ketones and alkenes, oxidation of sulfides to sulfoxides and sulfones, bayer‐villeger reaction, bromination and iodation of aniline and phenol derivatives, oxidative esterification, oxidative amidation of aromatic aldehydes, thiocyanation of aromatic compounds, and oxidation of pyridines, oxidation of secondary, allylic and benzylic alcohols. All the approaches were carried out under mild conditions and short reaction times and afforded the corresponding products in high yields.

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1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane as new oxidant for chemoselective and catalyst free oxidation of sulfides to sulfoxides and sulfones

Cited by 5 publications

References 42 publications

1,2‐Diphenyl‐1,1,2,2‐tetrahydroperoxyethane

1,2‐Diphenyl‐1,1,2,2‐tetrahydroperoxyethane

Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant

Urea‐2,2‐dihydroperoxypropane as a Novel and High Oxygen Content Alternative to Dihydroperoxypropane in Several Oxidation Reactions

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