1960
DOI: 10.1021/jo01075a626
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Notes- Reaction of 1-Bromo-2,3-epoxybutane with Phenol in the Presence of Boron Trifluoride

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Cited by 6 publications
(3 citation statements)
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“…In an acid-catalyzed system, the reaction can occur at both epoxy carbons and a mixture of isomers is obtained. 26 The general consensus is that in acid-catalyzed systems, the reaction proceeds via a so-called "borderline S N 2" mechanism, generating a primary alcohol as the major product, and secondary alcohols are generated via a S N 2 mechanism 26,51,52 as the minor product. In contrast, a base-catalyzed reaction proceeds primarily via a classic S N 2 mechanism and generates a secondary alcohol as the major product.…”
Section: Nuclear Magnetic Resonance Of Acid-and Base-catalyzed Model ...mentioning
confidence: 99%
“…In an acid-catalyzed system, the reaction can occur at both epoxy carbons and a mixture of isomers is obtained. 26 The general consensus is that in acid-catalyzed systems, the reaction proceeds via a so-called "borderline S N 2" mechanism, generating a primary alcohol as the major product, and secondary alcohols are generated via a S N 2 mechanism 26,51,52 as the minor product. In contrast, a base-catalyzed reaction proceeds primarily via a classic S N 2 mechanism and generates a secondary alcohol as the major product.…”
Section: Nuclear Magnetic Resonance Of Acid-and Base-catalyzed Model ...mentioning
confidence: 99%
“…Alkaline treatment of 2,3,6-tri-O-acety1-4-O-tosyl-/3-D-glucoside (Eq. 244) gives the corresponding deacetylated 3,4anhydro compound,l207* 1208 and methyl 4-O-tosyl-/3-~-glucoside and its 2,3-di-O-benzoyI derivative give methyl 3,4-anhydro-/3-~-glucoside.258 Although it had been reported previously723 that methyl 3,4,6-tri-O-acetyl-2-O-tosy1-/3-~-glucoside simply gives the expected 2,3-anhydro derivative, later work936 has shown simultaneous formation of a certain amount of the 3,4-epoxy sugar as well (Eq. 245).…”
Section: Ohmentioning
confidence: 99%
“…On the other, Naqvi and co-workers1216 reported failing to duplicate the previous work, acetylcyclopentane being the only recognizable product according to these authors. 244 Chapter I Thermal isomerization at 220" in the absence of catalyst,l749 or isomerization a t 60" in the presence of magnesium bromide,1216 gives a mixture of 2-methylcyclohexanone and acetylcyclopentane (Eq. 441).…”
Section: Ahy Hh3mentioning
confidence: 99%