A Family of New 1,2,4‐Trioxanes by Photooxygenation of Allylic Alcohols in Sensitizer‐Doped Polymers and Secondary Reactions.

Bartoschek, Anna; El-Idreesy, Tamer T.; Griesbeck, Axel G.; Hoeinck, Lars‐Oliver; Lex, Johann; Miara, Claus; Neudoerfl, Joerg M.

doi:10.1002/chin.200605169

Cited by 3 publications

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“…Vennerstrom (Scheme 66). Such peroxides were obtained by the interaction of α-hydroxyperoxides 183 with aldehydes 184 and ketones 186 [52,[164][165][166][167]. The resulting cyclic peroxides were tested in vitro for antimalarial activity against P. falciparum.…”

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confidence: 99%

Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

et al. 2022

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Organic peroxides are an important class of compounds for organic synthesis, pharmacological chemistry, materials science, and the polymer industry. Here, for the first time, we summarize the main achievements in the synthesis of organic peroxides by the action of Lewis acids and heteropoly acids. This review consists of three parts: (1) metal-based Lewis acids in the synthesis of organic peroxides; (2) the synthesis of organic peroxides promoted by non-metal-based Lewis acids; and (3) the application of heteropoly acids in the synthesis of organic peroxides. The information covered in this review will be useful for specialists in the field of organic synthesis, reactions and processes of oxygen-containing compounds, catalysis, pharmaceuticals, and materials engineering.

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confidence: 99%

Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

et al. 2022

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“…Depending on the nature of the olefinic target, valuable intermediates such as allylic hydroperoxides, endoperoxides (1,2‐dioxenes) and 1,2‐dioxetanes result from the reactions involving 1 O 2 via three principal classes— ene reaction, [2+2] and [2+4] cycloadditions (2,3). These transformations represent powerful protocols for introducing molecular oxygen in a highly specific fashion into organic compounds with wide applications in organic synthesis (2–4).…”

Section: Introductionmentioning

confidence: 99%

“…Usually, 1 O 2 is generated by an energy‐transfer mechanism after photoexcitation of a sensitizer dye molecule in the presence of ground‐state triplet oxygen, 3 O 2 (1–4). The reaction of 1 O 2 with the singlet ground state of organic molecules is so specialized that examples of spontaneous addition of 3 O 2 are rare.…”

Section: Introductionmentioning

confidence: 99%

UVA Self‐Photosensitized Oxygenation of β‐Ionone

Borsarelli

Mischne

La–Venia

et al. 2007

Photochem & Photobiology

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The steady-state UVA (350 nm) photolysis of (E)-beta-ionone (1) in aerated toluene solutions was studied by (1)H NMR spectroscopy. The formation of the 1,2,4-trioxane (2) and 5,8-endoperoxide (5) derivatives in the ratio of 4:1 was observed. Time-resolved laser induced experiments at 355 nm, such as laser-flash photolysis, photoacoustic and singlet oxygen (1)O(2) phosphorescence detection, confirmed the formation of the excited triplet state of 1 with a quantum yield Phi(T) = 0.50 as the precursor for the generation of singlet oxygen (1)O(2) (Phi(Delta) = 0.16) and the isomeric alpha-pyran derivative (3), which was a reaction intermediate detected by NMR. In turn, the reaction of (1)O(2) with 1 and 3 occurred with rate constants of 1.0 x 10(6) and 2.5 x 10(8) M(-1)s(-1) to yield the oxygenated products 5 and 2, respectively, indicating the relevance of the fixed s-cis configuration in the alpha-pyran ring in the concerted [2+4] cycloaddition of (1)O(2).

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Synthetic Approaches to Mono- and Bicyclic Perortho-Esters with a Central 1,2,4-Trioxane Ring as the Privileged Lead Structure in Antimalarial and Antitumor-Active Peroxides and Clarification of the Peroxide Relevance

et al. 2017

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The synthesis of 4-styryl-substituted 2,3,8-trioxabicyclo[3.3.1]nonanes, peroxides with the core structure of the bioactive 1,2,4-trioxane ring, was conducted by a multistep route starting from the aryl methyl ketones 1a–1c. Condensation and reduction/oxidation delivered enals 4a–4c that were coupled with ethyl acetate and reduced to the 1,3-diol substrates 6a–6c. Highly diastereoselective photooxygenation delivered the hydroperoxides 7a–7c and subsequent PPTS (pyridinium-p-toluenesulfonic acid)-catalyzed peroxyacetalization with alkyl triorthoacetates gave the cyclic peroxides 8a–8e. These compounds in general show only moderate antimalarial activities. In order to extend the repertoire of cyclic peroxide structure, we aimed for the synthesis of spiro-perorthocarbonates from orthoester condensation of β-hydroxy hydroperoxide 9 but could only realize the monocyclic perorthocarbonate 10. That the central peroxide moiety is the key structural motif in anticancer active GST (glutathione S-transferase)-inhibitors was elucidated by the synthesis of a 1,3-dioxane 15—with a similar substitution pattern as the pharmacologically active peroxide 11—via a singlet oxygen ene route from the homoallylic alcohol 12.

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A Family of New 1,2,4‐Trioxanes by Photooxygenation of Allylic Alcohols in Sensitizer‐Doped Polymers and Secondary Reactions.

Cited by 3 publications

References 0 publications

Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides

UVA Self‐Photosensitized Oxygenation of β‐Ionone

Synthetic Approaches to Mono- and Bicyclic Perortho-Esters with a Central 1,2,4-Trioxane Ring as the Privileged Lead Structure in Antimalarial and Antitumor-Active Peroxides and Clarification of the Peroxide Relevance

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