2007
DOI: 10.1016/j.molcata.2006.12.041
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Ammonium acetate catalyzed improved method for the regioselective conversion of olefins into halohydrins and haloethers at room temperature

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Cited by 47 publications
(26 citation statements)
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“…Our procedure for iodomethoxylation of alkenes allows simple and environmentally sustainable synthesis of important products 3 in high yields ( Table 1). Previously known methods for the preparation of -iodoethers 3 were based on the reactions of alkenes with non-recyclable reagents: N-iodosuccinimide [38][39][40], dichloroiodoisocyanuric acid [41], triiodoisocyanuric acid [42] N-iodosaccharin [43], ICl [44], I 2 [45], t-butyl or methyl hypoiodites [46], I(Py) 2 BF 4 [47], iodide/iodate [48], I 2 -H 2 O 2 [49], AgOTf [50], Ce (IV) salts [51], thallium salts [52,53], Pb (IV) salts [54], Cu (II) salts [55,56], and Hg (II) salts [57].…”
Section: Resultsmentioning
confidence: 99%
“…Our procedure for iodomethoxylation of alkenes allows simple and environmentally sustainable synthesis of important products 3 in high yields ( Table 1). Previously known methods for the preparation of -iodoethers 3 were based on the reactions of alkenes with non-recyclable reagents: N-iodosuccinimide [38][39][40], dichloroiodoisocyanuric acid [41], triiodoisocyanuric acid [42] N-iodosaccharin [43], ICl [44], I 2 [45], t-butyl or methyl hypoiodites [46], I(Py) 2 BF 4 [47], iodide/iodate [48], I 2 -H 2 O 2 [49], AgOTf [50], Ce (IV) salts [51], thallium salts [52,53], Pb (IV) salts [54], Cu (II) salts [55,56], and Hg (II) salts [57].…”
Section: Resultsmentioning
confidence: 99%
“…The halohydrination of a double bond has been widely reported using N-halogen species such as trichloroisocyanuric acid (TCCA), 11 tribromoisocyanuric acid (TBCA), 12 N-bromosuccinimide (NBS) 13,14 and N-chlorosuccinimide (NCS). 15 Our research focused on searching for an effective N-halogen reagent for the halohydrination of the ester 8.…”
Section: Resultsmentioning
confidence: 99%
“…Following reagents were prepared according to published protocols: 5,5′‐dibromo‐2,2′‐bithiophene ( 1 ), 4,4′‐dibromo‐5,5′‐bis[(1,1‐dimethylethyl)dimethylsilyl]‐2,2′‐bithiophene ( 2 ), trimethyl[(3 Z )‐4‐(methylthio)‐3‐penten‐1‐yn‐1‐yl]silane ( 4a ), 3‐bromo‐2‐iodothiophene ( 5 ), 2,3‐dibromo‐5‐iodothiophene ( 25 ) (adapted), N , N′ ‐dimethoxy‐ N , N′ ‐dimethylsuccinamide . 2,3‐Dihydro‐5,7‐diiodothieno[3,4‐ b ]‐1,4‐dioxin and 2,5‐diiodo‐3,4‐dimethoxythiophene were prepared by iodination according to a published procedure . Common anhydrous solvents were prepared by filtration through drying columns (PURESOLV‐plant by it‐innovative technology inc.).…”
Section: Methodsmentioning
confidence: 99%