New research progress on 114214-49-2 in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. In an article, author is Griffith, Gerry A., once mentioned the application of 114214-49-2, Application In Synthesis of tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, Name is tert-Butyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, molecular formula is C9H15NO3, molecular weight is 185.22, MDL number is MFCD08691407, category is dioxole. Now introduce a scientific discovery about this category.
Difluorinated alkenoate ethyl 3,3-difluoro-2-(N, N-diethylcarbamoyloxy)-2-propenoate reacts rapidly and in high yield with furan and a range of substituted furans in the presence of a tin(IV) catalyst. Non-fluorinated congener 2-(N, N-diethylcarbamoyloxy)-2-propenoate fails to react at all under the same conditions. These reactions have been explored using density functional theory (DFT) calculations. They reveal a highly polar transition state, which is stabilized by the Lewis acid catalyst SnCl4 and by polar solvents. In the presence of both catalyst and solvent, a two-step reaction is predicted, corresponding to the stepwise formation of the two new carbon-carbon bonds via transition states which have similar energies in all cases. Our experimental observations of the lack of reaction of the non-fluorinated dienophile, the stereochemical outcomes, and the rate acceleration accompanying furan methylation are all well predicted by our calculations. The calculated free energy barriers generally correlate well with measured reaction rates, supporting a reaction mechanism in which zwitterionic character is developed strongly. An in situ ring opening reaction of exo-cycloadduct ethyl exo-2-(N, N-diethylcarbamoyloxy)-3,3-difluoro-7-oxabicyclo[2.2.1] hept-5-enyl-2-endo-carboxylate, which results in the formation of cyclic carbonate ethyl 4,4-difluoro-5-hydroxy-2-oxo-5,7a-dihydro-4H-benzo[1,3] dioxole-3a-carboxylate by a Curtin-Hammett mechanism, has also been examined. Substantial steric opposition to Lewis acid binding prevents carbonate formation from 2-substituted furans.
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Reference:
1,3-Benzodioxole – Wikipedia,
,Dioxole | C3H4O2 – PubChem