Reactivity of 4-R-1,2,4-triazoline-3,5-diones towards nitrone spin-traps: spectral study of the reaction with 5,5-dimethylpyrroline-N-oxide

Alstanei, Ana-Maria; Risi, Florence; Carles, Micheline; Aycard, Jean‐Pierre; Pizzala, L.; Volanschi, Elena

doi:10.1039/a902759i

Cited by 5 publications

(2 citation statements)

References 9 publications

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“…The IR and NMR spectra agree with the formation of a single reaction product, corresponding to the structure 5, and so 6 is the structure assigned to the spin adduct (see Scheme 4), which confirms the existence of urazolyl radicals in the MTAD solutions at room temperature. The reaction between 4-R-1,2,4-triazoline-3,5-diones with DMPO was investigated [29] and the results were rationalised in terms of a reaction sequence in which the spin adduct is formed by a modified version of the Forrester-Hepburn mechanism. [30] Figure 2.…”

Section: Esr Experimentsmentioning

confidence: 99%

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

et al. 2000

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The photoaddition of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (4‐MTAD) with a wide variety of acyclic, cyclic and crown aliphatic ethers has been investigated. Monochromatic (λ = 514.5 nm) or polychromatic (λ ≥ 310 nm) irradiations give identical mono‐urazolyl ethers as reaction products. Unsymmetrical acyclic ethers afford a mixture of the two α and α′ mono‐urazolyl ethers. In the case of 12‐crown‐4, mono and di‐substituted products are obtained. ESR experiments and quantum calculations at the AM1 and 6‐31G* levels were performed and a possible reaction mechanism is proposed in which the most probable photochemical process is the H‐abstraction leading to a urazolyl radical.

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Section: Esr Experimentsmentioning

confidence: 99%

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

et al. 2000

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“…Although he reported this oxidation method to be the best one of those investigated, no pure 4-phenyltriazolinedione could be isolated. Only one other claim, over a century later, can be found of a lead(IV) oxide-mediated urazole oxidation . Most likely, the presence of redox-active metal ions is actually expected to contribute to a rapid decomposition of TAD compounds, which explains why these methods are much less popular than the preceding three types (sections –).…”

Section: Oxidation Of 4-substituted Urazoles To Their Corresponding 1...mentioning

confidence: 99%

Triazolinediones as Highly Enabling Synthetic Tools

et al. 2016

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Triazolinediones (TADs) are unique reagents in organic synthesis that have also found wide applications in different research disciplines, in spite of their somewhat "exotic" reputation. In this review, we offer two case studies that demonstrate the possibilities of these versatile and reliable synthetic tools, namely, in the field of polymer science as well as in more recently emerging applications in the field of click chemistry. As the general use of triazolinediones has always been hampered by the limited commercial and synthetic availability of such reagents, we also offer a review of the available TAD reagents, together with a detailed discussion of their synthesis and reactivity. This review thus aims to serve as a practical guide for researchers that are interested in exploiting and further developing the exceptional click-like reactivity of triazolinediones in various applications.

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12.3.1.3 Trisubstituted pyrrolidinyl-N-oxyls

Alberti

Landolt-Börnstein - Group II Molecules and Radicals

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Reactivity of 4-R-1,2,4-triazoline-3,5-diones towards nitrone spin-traps: spectral study of the reaction with 5,5-dimethylpyrroline-N-oxide

Cited by 5 publications

References 9 publications

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

Photoaddition of Aliphatic Ethers to 4-Methyl-1,2,4-triazoline-3,5-dione: Application to the Synthesis of Functionalized Crown Ethers and Mechanism

Triazolinediones as Highly Enabling Synthetic Tools

12.3.1.3 Trisubstituted pyrrolidinyl-N-oxyls

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