The Radiation Chemistry of Isopropyl Acetate and Isopropenyl Acetate

Newton, Amos S.; Strom, Peter O.

doi:10.1021/j150559a007

Cited by 20 publications

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“…Previous investigations of the mass spectra of esters have been limited primarily to methyl (1,18) and aromatic esters (12). Newton and Strom have compared the spectra of isopropyl and isopropenyl acetate (22). Several investigations of the formation of rearrangement ions in mass spectra have been reported (1, 6, 9,10,15,17, 21, 27).…”

mentioning

confidence: 99%

Mass Spectra of Esters. Formation of Rearrangement Ions

Sharkey¹,

Shultz²,

Friedel³

1959

Anal. Chem.

107

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mentioning

confidence: 99%

Mass Spectra of Esters. Formation of Rearrangement Ions

Sharkey¹,

Shultz²,

Friedel³

1959

Anal. Chem.

107

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“…[118] Poly-isopropanol (PiPOH) was then obtained by hydrolysis of the acetyl moieties (Scheme 34, a). The effects of helium ions irradiation towards liquid iPAc and isopropyl acetate have been studied at room temperature and at 80 °C by Newton et al [119] It was found a factor of thirty higher "polymer" yield when iPAc was used in place of isopropyl acetate, indicating that the polymerization occurs through the double bond. [119] iPAc was also investigated for various copolymerization processes.…”

Section: Reactions Of the C=c Double Bondmentioning

confidence: 99%

“…The effects of helium ions irradiation towards liquid iPAc and isopropyl acetate have been studied at room temperature and at 80 °C by Newton et al [119] It was found a factor of thirty higher "polymer" yield when iPAc was used in place of isopropyl acetate, indicating that the polymerization occurs through the double bond. [119] iPAc was also investigated for various copolymerization processes. Vinyl chloride and iPAc were emulsion copolymerized in sealed tubes at 45°C.…”

Section: Reactions Of the C=c Double Bondmentioning

confidence: 99%

Isopropenyl Esters (iPEs) in Green Organic Synthesis

Rigo

Masters

Maschmeyer

et al. 2022

Chemistry A European J

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The need for greener compounds able to replace conventional ones with similar reactivity is crucial for the development of sustainable chemistry. Isopropenyl esters (iPEs) represent one eco-friendly alternative to acyl halides and anhydrides. This review provides a comprehensive overview of the preparation methodologies and reported synthetic applications of iPEs and, in particular, of isopropenyl acetate (iPAc). Intriguingly, the presence of a C=C double bond adjacent to the ester functionality makes iPEs appealing in different chemoselective organic synthesis transformations. For instance, the acyl moiety is suitable for transesterification reactions in presence of different heteroatom-based nucleo-philes (CÀ , OÀ , NÀ , SÀ , SeÀ ); these reactions are irreversible thanks to the formation of acetone, obtained upon keto-enol tautomerization of the prop-1-en-2-ol (isopropenyl) leaving group. Similarly, the unsaturation contained in the isopropenyl synthon could be selectively exploited in organic synthesis for electrophilic and/or radical additions as well as in metal-catalyzed cross-coupling reactions. To conclude, iPEs recently found major interest in the direct modification of biomass (i.e. lignin or cellulose) and in the implementation of tandem reactions of esterification-acetalization by exploiting the co-formation of acetone during the reaction.

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Chemische Wirkung ionisierender Strahlen 3. Kernstrahlenchemie halogen‐ und sauerstoff‐haltiger Verbindungen

Henglein¹

1960

Angewandte Chemie

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lonisierende Strahlen erzeugen in Gegenwart funktioneller Gruppen Stoffe niedrigerer und hoherer Molekulargewichte durch h d e r u n g e n an den funktionellen Gruppen selbst oder an den Kohlenwasserstoff-Resten. Ein Teil der Strahlenreaktionen verlauft uber thermalisierte freie Radikale; zusatzlich treten schnelle, diffusionskontrollierte Prozesse wie Reaktionen ,,heiOer" Radikale und lonen-Reaktionen auf. Massenspektrometrische Beobachtungen fuhrten zur Entdeckung langlebiger aktivierter Komplexe von Ion-Molekul-Reaktionen in Alkylhalogeniden und von Reaktionen negativer lonen. Mehrere Strahlenreaktionen sind fur die praparative Chemie von Interesse, z. B. die Kondensation von Aminen und Hydroxy-Verbindungen zu Dimeren oder hoheren Polymeren, die Synthese von organischen Dichlorphosphinen, Trichlorsilanen und Dichlorarsinen aus Mischungen gesattigter oder ungesattigter Kohlenwasserstoffe mit anorganischen Polychloriden und die Synthese von Nitroso-Verbindungen aus organischen Flussigkeiten und Stickstoffmonoxyd. Einleitung T wird um so groBer, je grol3er die Zahl C( = 3N-6 der Freiheitsgrade des N-atomigen Komplexes und je groBer Ei ist. Der Yomplex IaUt sich im Massenspektrometer beobach-6) M . Burton u.

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The Radiation Chemistry of Isopropyl Acetate and Isopropenyl Acetate

Cited by 20 publications

References 0 publications

Mass Spectra of Esters. Formation of Rearrangement Ions

Mass Spectra of Esters. Formation of Rearrangement Ions

Isopropenyl Esters (iPEs) in Green Organic Synthesis

Chemische Wirkung ionisierender Strahlen 3. Kernstrahlenchemie halogen‐ und sauerstoff‐haltiger Verbindungen

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