- Generation of ortho-quinone methides upon thermal extrusion of sulfur dioxide from benzosultones
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3H-1,2-Benzoxathiole 2,2-dioxides (benzosultones) undergo thermal extrusion of sulfur dioxide to form ortho-quinone methides that enter Diels-Alder reaction with maleimides to form chroman 2,3-dicarboxylic acid derivatives.
- Wojciechowski, Krzysztof,Dolatowska, Karolina
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- NUCLEOPHILIC SUBSTITUTION AT SULPHUR. COMPLEXES OF SULTONES WITH CHLORIDE AND BROMIDE IONS
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2-Hydroxy-3,5-dinitrotoluene-α-sulphonic acid sultone, 1, reacts with Cl(-) in nitrobenzene or acetonitrile yielding 2-hydroxy-3,5-dinitrotoluene-α-sulphonyl chloride.The reaction proceeds via the formation of an ion-molecule pair.Similar complexes are formed with the corresponding mononitro and unsubstituted sultones, 4 and 5, which do not undergo nucleophilic substitution.The complexes are detected by NMR since the methylene protons of the sultones in the complexes are displaced by more than 1 ppm to lower field because of the adjacent negative charge of the halide ion.
- Gambarotta, Sandro,Isola, Mauro,Senatore, Lucio,Ciuffarin, Ennio
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p. 297 - 300
(2007/10/02)
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