1,3-Dipolar Cycloadditions, 99. Nitrones and Thiones: Cycloadditions and Surprising Metathesis Reactions†‡
作者： Henry Giera , Rolf Huisgen
DOI: 10.1002/JLAC.199719970809
关键词: Metathesis 、 Nitrone 、 Salt metathesis reaction 、 Medicinal chemistry 、 Cycloaddition 、 Steric effects 、 Chemistry 、 Photochemistry 、 Alicyclic compound 、 Benzaldehyde 、 Thiobenzophenone
摘要: Nitrone 4 combines with alicyclic thioketones at room temp. affording 1,4,2-oxathiazolidines. Steric hindrance in both reactants affects the cycloaddition/cycloreversion equilibria, but mobility is still high; low π-LUMO energies of CS are responsible for superdipolarophilic character. and thiobenzophenone enter into a metathesis reaction which was traced back to sulfhydrogenolysis pathway; H2S acts as catalyst. An analogous between nitrone benzaldehyde involves hydrolysis.
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