Selective Reduction of the CarbonBromine Bond in Bromo Epoxides
TL;DR: The controlledpotential electrolysis of various substituted bromo epoxides in acetonitrile at a mercury pool electrode led to selective reduction of the carbon-bromine bond affording the respective epoxide products in 80-90% yield.
About: This article is published in Tetrahedron Letters.The article was published on 1992-03-10. It has received 6 citations till now. The article focuses on the topics: Selective reduction & Epoxide.
Citations
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TL;DR: Evidence is suggested that the reduction of bromostyrene proceeds differently than previously described, and the hydrodehalogenations described herein are amine free and can be carried out in THF with relatively low loads of catalyst.
24 citations
TL;DR: Electrochemical methods provide for selective reduction of vinyl iodides over vinyl bromides, with better yields than analogous tin methodology.
Abstract: Several vinyl halides previously used in inositol syntheses were subjected to electrochemical reduction. The unreactivity of allylic alcohols or allylic ethers at the applied potentials allowed the...
23 citations
TL;DR: In this paper, the influence of various parameters including solvent, base and temperature on the reaction between carbazole and epoxides was studied, which led to the development of a regioselective ring-opening mechanism.
Abstract: The influence of various parameters including solvent, base and temperature on the reaction between carbazole and epoxides was studied. This led to the development of a regioselective ring-opening ...
2 citations
DOI•
29 Aug 2017TL;DR: Reduction============Cyclic Alkanes============Arenes============Alkenes======Alkynes======Organic Halides======Amines and Derivatives======Nitro Compounds======Ethers======Alcohols and Phenols======Sulfur Compounds ``(Selenium and Tellurium Compounds")======Aldehydes and Ketones======Acetals======Carboxylic Acids======
Abstract: Reduction
Cyclic Alkanes
Arenes
Alkenes
Alkynes
Organic Halides
Amines and Derivatives
Nitro Compounds
Ethers
Alcohols and Phenols
Sulfur Compounds
Selenium and Tellurium Compounds
Aldehydes and Ketones
Acetals
Carboxylic Acids
Acid Halides
Anhydrides
Esters and Lactones
Nitriles
Isonitriles
Keywords:
alkanes;
arenes;
cycloalkanes;
reduction;
decarbonylation;
dehalogenation;
deamination;
desulfuration;
hydrogenation catalysts;
chiral ligands;
metal hydrides
1 citations
TL;DR: Polarographic and cyclic voltammetric studies of bromohydrins in acetonitrile showed a single diffusion-limited two-electron irreversible cathodic wave/peak followed by chemical transformations as discussed by the authors.
References
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TL;DR: In this paper, the anodic oxidation of aliphatic sulfides has been investigated, using cyclic voltammetry and controlled potential electrolysis, considering the effects of variation of water content and of type of supporting electrolyte.
Abstract: The anodic oxidation of aliphatic sulfides has been investigated, using cyclic voltammetry and controlled potential electrolysis. Reactions of dimethyl sulfide in acetonitrile have been studied in detail, considering the effects of variation of water content and of type of supporting electrolyte. With as much as 1% water in , dimethyl sulfide is completely oxidized to dimethyl sulfone. In anhydrous , the products are and . It is suggested that the electrochemical reaction involves formation of protons and , which condenses with to form . When perchlorate is present as supporting electrolyte, it is involved in a slow chemical reaction which produces Cl−, , and . The reaction of benzyl methyl sulfide is very similar, leading to benzaldehyde and .
71 citations
TL;DR: In this article, a novel access to β-hydroxy carbonyl compounds from the corresponding α,β-epoxy carbonyls compounds has been attained through the recyclable use of diphenyl diselenide or Diphenyl ditelluride as an electroreduction mediator in a MeOH-NaClO 4 -(Pt) system.
Abstract: A novel access to β-hydroxy carbonyl compounds from the corresponding α,β-epoxy carbonyl compounds has been attained through the recyclable use of diphenyl diselenide or diphenyl ditelluride as an electroreduction mediator in a MeOH-NaClO 4 -(Pt) system α,β-Epoxy ketones are converted to the corresponding aldols in the presence of malonic esters Similarly, α,β-epoxy esters and nitriles can be reduced to the corresponding β-hydroxy compounds in the presence of acetic acid
44 citations
TL;DR: In this article, the electrochemical behavior of the epoxides having the structure with R being an aromatic ring (or any unsaturated system) is described in the couple: DMF-tetraalkylammonium salts on a mercury cathode.
39 citations
26 citations