Kinetics of Thermal and Hydrolitic Decomposition of 1,3,4-Dioxazol-2-one Derivatives
The synthesis of model compounds 5 and 6 for the homopolymers of vinyl and isopropenydioxazol-2-ones is described.These compounds are hydrolyzed to hydroxamic acids which can be estimated colorimetrically by complexation with Fe3+.The hydrolitic rates have been determined and the thermolysis rates were followed by measuring undecomposed dioxazolones by the colorimetric method.The isopropyldioxazolone was 100 times faster in thermal decomposition in the bulk than the tert-butyl-substituted one and this difference is reduced in presence of polar solvents.The resulrsexplain the previously observed differences in the thermal stability of the two polymers.
Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis
A rhodium(III)-based catalytic system has been used to develop a C?H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C?H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium-catalyzed aldehydic C?H amidation.
Bellière-Baca, Virginie,Clavier, Hervé,Hérault, Damien,Massouh, Joe,Petrelli, Antoine
supporting information
(2022/01/06)
Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
Sulfur imidations by light-induced ruthenium-catalyzed nitrene transfer reactions
N-Acyl nitrenes have been generated from a range of heterocyclic precursors, and their applications in light-induced ruthenium-catalyzed sulfur imidations have been studied. Analyzing the reaction scope and determining the structural requirements of the in situ formed electrophilic nitrogen species for effective nitrene transfer allowed a mechanistic scheme to be proposed. The mechanistic conclusions were substantiated by the identification of potential intermediates.
Bizet, Vincent,Bolm, Carsten
supporting information
p. 2854 - 2860
(2015/07/01)
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