Notes- Reaction of 1-Bromo-2,3-epoxybutane with Phenol in the Presence of Boron Trifluoride

Bridger, Robert F.; Russell, Robert R.

doi:10.1021/jo01075a626

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%

Acid‐ and base‐catalyzedepoxy‐phenolthermosets from catechol, resorcinol and hydroquinone: Astructure–propertystudy

Choudhury

Houston

Mason

et al. 2021

J of Applied Polymer Sci

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In order to better understand the design rules of epoxy–phenol thermosets we will report on the chemistry and (thermo)mechanical properties of cured epoxy–phenol thermoset films. Ortho‐, meta‐ and para‐isomers of dihydroxybenzene (DHB) were reacted with the diglycidyl ether of bisphenol A (DGEBA) in the presence of an acid catalyst or triphenylphosphine (PPh3). The glass transition temperatures (Tg) of the cross‐linked films decreases in the order of meta‐ (Tg = 115°C) > ortho‐ (Tg = 102°C) > para‐DHB (Tg = 96°C) as measured by differential scanning calorimetry. Uniaxial tensile testing of cross‐linked films showed excellent stress–strain behavior. The average ultimate strength values ranged from 65 to 82 MPa and the average values of the strain‐at‐break ranged from 4.8% to 6.9% at 25°C for all cross‐linked films. When a PPh3 was used, the network properties were profoundly different. The base catalyzed thermoset of DGEBA and meta‐DHB shows a Tg of 85°C, which is 30°C lower than the Tg of the acid‐catalyzed analog. Tensile films appear to be more ductile, as they exhibit a strain‐at‐break of 20%. The results of this study confirm that simple dihydroxybenzene hardeners can be used to prepare cross‐linked films with excellent thermomechanical properties.

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Section: Nuclear Magnetic Resonance Of Acid-and Base-catalyzed Model ...mentioning

confidence: 99%

Acid‐ and base‐catalyzedepoxy‐phenolthermosets from catechol, resorcinol and hydroquinone: Astructure–propertystudy

Choudhury

Houston

Mason

et al. 2021

J of Applied Polymer Sci

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“…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%

Ethylene Oxides

Rosowsky¹

1964

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Zur Relativen Reaktivität der Epoxid‐ und Halogengruppe in Epihalogenhydrinen bei der basenkatalysierten Reaktion mit Hydroxyverbindungen

et al. 1972

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Die basenkatalysierte Reaktion von Epihalogenhydrinen mit Hydroxyverbindungen kann theoretisch primär unter Aufspaltung des Epoxidringes (Weg I), Substitution des Halogens (Weg II) oder gleichzeitig nach I und II ablaufen. Versuche mit [3‐14C] markierten Epihalogenhydrinen und verschiedenen Hydroxyverbindungen zeigen, daß der Reaktionsverlauf uneinheitlich ist und stark von den Reaktionsbedingungen abhängt; wäßriges alkalisches Medium begünstigt Weg I, wasserfreies Weg II. Der Temperatureinfluß ist im Bereich von 25° bis 75° gering. Phenol z. B. reagiert in wäßriger Natronlauge bei 25° sowohl mit Epichlor‐ als auch Epibromhydrin fast quantitativ gemäß I. Bei 75° tritt Substitution bei Epichlorhydrin zu 5%, bei Epibromhydrin zu 10% ein; in wasserfreiem Medium steigt der Substitutionsanteil bei Epichlorhydrin auf 11%, bei Epibromhydrin auf 69%.

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Notes- Reaction of 1-Bromo-2,3-epoxybutane with Phenol in the Presence of Boron Trifluoride

Cited by 6 publications

References 0 publications

Acid‐ and base‐catalyzedepoxy‐phenolthermosets from catechol, resorcinol and hydroquinone: Astructure–propertystudy

Acid‐ and base‐catalyzedepoxy‐phenolthermosets from catechol, resorcinol and hydroquinone: Astructure–propertystudy

Ethylene Oxides

Zur Relativen Reaktivität der Epoxid‐ und Halogengruppe in Epihalogenhydrinen bei der basenkatalysierten Reaktion mit Hydroxyverbindungen

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