Ozone Oxidation of Sulfides and Sulfoxides

Maggiolo, Allison; Blair, E.

doi:10.1021/ba-1959-0021.ch030

Cited by 17 publications

(8 citation statements)

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“…When the removal of the propenyl group was carried out before the S‐oxidation, conversion of the sulfide to the corresponding sulfoxides 24 and 25 took place. As reported for other sulfides before, the ozone mediated oxidation stopped at the sulfoxide level at the low temperature required for the removal of the propenyl group. The crude product was oxidized further to sulfones 22 and 23 by treatment with oxone.…”

Section: Resultssupporting

confidence: 69%

The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

Paulsen

Gundersen

2020

Eur J Org Chem

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Agelasine F (also known as ageline A) is a diterpene-adenine hybrid natural product isolated from marine sponges (Agelas species) and this compound is known to display cytotoxic activity against a variety of cancer cell lines as well as microorganisms. We herein report the first total synthesis of (-)-agelasine F. The commercially available and inexpensive monoterpenoid (S)-carvone was found to be a highly suitable starting material for the construction of the terpenoid part [a]

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Section: Resultssupporting

confidence: 69%

The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

Paulsen

Gundersen

2020

Eur J Org Chem

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“…The reaction of ozone with heteroatom compounds containing free electron pairs or dorbitals has come under increasing study in recent years (1)(2)(3)(4)(5). In most cases the final products do not incorporate all three oxygen atoms of the ozone and variously formulated intermediates have been proposed.…”

mentioning

confidence: 99%

The Rate Constants for the Reactions of Ozone with Triphenylphosphite and Triphenylphosphine

Разумовский¹,

Mendenhall²

1973

Can. J. Chem.

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The stoichiometry and rate constants for the reaction of triphenylphosphite and triphenylphosphine with ozone were measured at several temperatures. The rate was first order in each reactant, with k = (3f 1) x lo4 and ( 5 f 2 ) x lo3 M -' s-' , respectively, for the reaction of ozone with triphenylphosphine and triphenylphosphite (2,4-dimethylhexane, -9 0 ) . The reaction of ozone with triphenylphosphite has a low activation energy in carbon tetrachloride. The stoichiometry was 1:l for both compounds under these conditions. La stoechiomCtrie et les constantes de vitesse de la reaction entre le triphCnylphosphite et la triphinylphosphine avec I'ozone ont Bte mesurees a diverses temptratures. La vitesse est du premier ordre pour chaque reactant avec k = ( 3 i 1) x loJ et ( 5 2 2) x lo3 M -' s-' respectivement pour la triphCny1-phosphine et le triphCnylphosphite (dimithyl-2,4-hexane, -90"). La reaction de I.ozone sur le triphinylphosphite possede une faible energie d'activation dans le tCtrachlorure de carbone. La stoechiometrie est de 1 :1 pour les deux composes dans ces conditions.[Traduit par le journal]Can.

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“…• Absorbing species O 2 : initiating oxidation of TP by O (reactions (3) and/or (4)) e.g., 20,34,35 • Absorbing species O 2 : initiating oxidation of TP by O 3 , 33,54 • Absorbing species TP: oxidation by addition of O 2 to intermediate radicals generated by the photolysis of TP (reaction (13)), 27 • Absorbing species H 2 O: initiating oxidation of TP by HO • (reactions (11) and ( 12)). 39,55 Fig.…”

Section: Efficiency Of the Vuv-photochemically Initiated Oxidative De...mentioning

confidence: 99%

“…All three oxidants (O, O 3 and HO • ) also react with the S-function of TP [33][34][35]54,57 to form the corresponding sulfoxide (thiophene 1-oxide ( 15)) and sulfone (thiophene 1,1-dioxide ( 16), Scheme 4), the latter being assumed to eliminate SO 2 in the course of an oxidative degradation. SO 2 -analyses exhibit…”

Section: Efficiency Of the Vuv-photochemically Initiated Oxidative De...mentioning

confidence: 99%

Continuous process of the vacuum ultraviolet- (VUV-) photochemical oxidation of thiophene in the gas phase

Andriampanarivo

Köhler

López‐Gejo

et al. 2015

Photochem Photobiol Sci

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Thiophene was taken as a model compound for investigations on the efficiency of a continuous process of the vacuum-ultraviolet- (VUV-) photochemically initiated oxidation and mineralization of sulfur containing organic compounds in the gas phase. In the presence of molecular oxygen, atomic oxygen and ozone were photochemically generated and are assumed to initiate or participate in the (thermal) oxidation network. Addition of water vapor for an additional initiation of the oxidation by hydroxyl radicals did not accelerate the process. For comparison, thiophene was exposed to ozone and oxidized under otherwise the same experimental conditions, but complete mineralization was only found in the photochemical process and for relatively small concentrations of the substrate. The result may be explained by low rates of secondary thermal reactions of a number of identified intermediate products. Combining already published results and mechanistic hypotheses with the results of the present work, pathways of oxidative degradation are proposed. The photolysis of thiophene in molecular nitrogen confirmed earlier findings.

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Ozone Oxidation of Sulfides and Sulfoxides

Cited by 17 publications

References 0 publications

The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

The Rate Constants for the Reactions of Ozone with Triphenylphosphite and Triphenylphosphine

Continuous process of the vacuum ultraviolet- (VUV-) photochemical oxidation of thiophene in the gas phase

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