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Beilstein J. Org. Chem. 2016, 12, 110–116, doi:10.3762/bjoc.12.12
Graphical Abstract
Scheme 1: Oxidation of SF5-anisole and phenol. 19F NMR yields are shown (isolated yields in parentheses).
Scheme 2: Proposed mechanism for the formation of 3 and 4 from SF5 aromatics 1 and 2.
Scheme 3: Oxidation of anisole 10 and phenol 11. 19F NMR yields are given.
Scheme 4: Synthesis of para-benzoquinone 12 and oxidation to maleic acid 4. 19F NMR yields are shown, in pare...
Scheme 5: Catalytic hydrogenation and Diels–Alder reaction of benzoquinone 12.
Figure 1: Optimized geometries of transition states of Diels–Alder reaction of cyclopentadiene with 12. Selec...
Scheme 6: Decomposition of 3 in water.
Scheme 7: Formation of acids 5, 18 and 19 from lactone 3.
Scheme 8: Synthesis of maleic anhydride 20 and Diels–Alder adducts 21.
Scheme 9: Reaction of maleic acid 4 with diazomethane.
Scheme 10: Decarboxylation of maleic acid 4 to acrylic acid 23 in DMSO and the preparation of deuterium labell...