Electrochemical behavior of N-oxyphthalimides: Cascades initiating self-sustaining catalytic reductive N-O bond cleavage was written by Syroeshkin, Mikhail A.;Krylov, Igor B.;Hughes, Audrey M.;Alabugin, Igor V.;Nasybullina, Darya V.;Sharipov, Mikhail Yu.;Gultyai, Vadim P.;Terent’ev, Alexander O.. And the article was included in Journal of Physical Organic Chemistry in 2017.Product Details of 58585-84-5 This article mentions the following:
N-oxyphthalimides are stable and easily accessible compounds that can produce O radicals upon 1-electron reduction The authors present a systematic study of electrochem. properties of N-oxyphthalimide derivatives (PI-ORs) in DMF by cyclic voltammetry. In all cases, electron transfer to the substrate leads to decomposition of the intermediate radical anion via the N-O bond cleavage. In the case of benzyloxyphthalimide or its derivatives containing electron-donating substituents, reductive electron transfer induces the chain decomposition of the substrate to phthalimide (PI) radical-anion and the corresponding carbonyl compound The PI radical-anion product is a powerful reductant that can transfer an electron to the reactant PI-OR, thus establishing a catalytic cycle for reductive N-O scission. This self-catalytic process is reflected in a considerable decrease in the reduction current for the substrate (<1e–/mol.). By contrast, reductive fragmentations of benzyl derivatives containing electron-withdrawing substituents in the aromatic ring or at the benzylic position, as well as tosyl and alkyl derivatives, occur via a 1-electron mechanism. A sequence of N-O and C-C scissions was engineered to support the intermediacy of O-centered radicals in these processes. In the experiment, the researchers used many compounds, for example, 1,3-Dioxoisoindolin-2-yl benzoate (cas: 58585-84-5Product Details of 58585-84-5).
1,3-Dioxoisoindolin-2-yl benzoate (cas: 58585-84-5) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. More than 200 indole derivatives have already been marketed as drugs or are under advanced stages of clinical trials.Product Details of 58585-84-5
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles