- Catalytic thia-Sommelet-Hauser rearrangement: Application to the synthesis of oxindoles
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A series of 3-arylthio-1,3-disubstituted-oxindoles were prepared in good yields by the reaction of α-diazocarbonyl compounds and sulfenamides. The reaction involves a Rh-catalyzed thia-Sommelet-Hauser-type rearrangement.(Figure Presented)
- Li, Yuye,Shi, Yi,Huang, Zhongxing,Wu, Xinhu,Xu, Pengfei,Wang, Jianbo,Zhang, Yan
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supporting information; experimental part
p. 1210 - 1213
(2011/04/27)
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- THERMAL REACTIVITY OF 4'SUBSTITUTED- AND 4'-SUBSTITUTED-2-PHENYL-BENZENESUPHENANILIDES
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The thermal decomposition of 4'-nitro, 4'-H, and 4'-methoxy-benzenesulphenanilides in benzene and/or furan, and of 4'-substituted-2-phenylbenzenesulphenanilides ( 1d-1f ) in benzene, was found to proceed by two distinct pathways: ( i ) nucleophilic displacement by furan and/or another sulphenanilide unit and ( ii ) homolytic S-N bond fission to give sulphenyl and anilino radicals.An increase in the electron-withdrawning capability of the 4'-substituted favours the ionic pathway, whwreas the radical pathway is favoured by an increase in the reaction temperature.
- Benati, Luisa,Montevecchi, Pier Carlo,Spagnolo, Piero
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