Untersuchungen zur Regioselektivität der anodischen Cyclisierung von 1,2‐Dioximen zu unsymmetrisch substituierten Furoxanen

Jugelt, W.; Tismer, Michael; Rauh, Maria

doi:10.1002/zfch.19830230115

Cited by 8 publications

(3 citation statements)

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“…It was shown that the anti-conformation (140a) resulted in a 50/50 racemic mixture of stereoisomers (143a and 143b), whereas the amphi-conformation (140b) resulted in a 100% yield of a single isomer (143b) (Scheme 17). 177 Niyazymbetov et al further confirmed these observations and asserted that the dioxome must go through an iminoxyl radical intermediate (141). 178 The authors showed that the iminioxyl radical must be formed and that 141 is more easily oxidized (E 1/2 = 0.42−0.54 V) than the oxime (E 1/2 = 1.27− 1.85).…”

Section: N Heterocyclesmentioning

confidence: 99%

“…From their studies, they detailed a possible reaction mechanism in which 175 is cathodically reduced to generate a hydroxylamine intermediate (176). Two-electron anodic oxidation of 176 yields a nitroso intermediate (177). The nitroso substituent then undergoes 1,5-intramolecular cyclization with the adjacent azo bridge to generate 178.…”

Section: N Heterocyclesmentioning

confidence: 99%

“…Cationic species 142 then undergoes 1,5-intramolecular cyclization to generate a furoxan ( 143 ) (Scheme ). Juglet also studied the effect of the regioselectivity of the glyoxime on the resulting furoxan. It was shown that the anti -conformation ( 140a ) resulted in a 50/50 racemic mixture of stereoisomers ( 143a and 143b ), whereas the amphi -conformation ( 140b ) resulted in a 100% yield of a single isomer ( 143b ) (Scheme ).…”

Section: Nitrogen-rich Heterocycle Formationmentioning

confidence: 99%

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Electrochemical Synthesis of High-Nitrogen Materials and Energetic Materials

Yount

Piercey

2022

Chem. Rev.

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Electrochemical synthesis is a valuable method for the preparation of molecules. It is innately eco-friendly, as potentially hazardous oxidation and reduction agents are replaced with electrochemical potentials. Electrochemistry is commonly applied globally in the synthesis of numerous chemicals, but the energetic materials field lags in this regard. In this review, we endeavor to cover the entire history of synthetic electrochemistry for the preparation of energetic materials and detail the electrochemical transformations of high-nitrogen materials that are relevant for the preparation of new energetic molecules. We hope this review serves as a starting point to inform those involved in synthetic energetic materials chemistry, and those interested in other applications of high-nitrogen molecules, about the environmentally friendly electrochemical methods available for such compounds.

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Section: N Heterocyclesmentioning

confidence: 99%

Section: N Heterocyclesmentioning

confidence: 99%

Section: Nitrogen-rich Heterocycle Formationmentioning

confidence: 99%

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