A new reaction of phosphorylated N-sulfonylimines with hydrophosphoryl agents involving C → N transfer of phosphoryl groups |
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Authors: | Yuliya V Rassukana Kateryna O Davydova Anatolii D Sinitsa |
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Affiliation: | Institute of Organic Chemistry, National Academy of Sciences, Kyiv 02094, 5 Murmans'ka Street, Ukraine |
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Abstract: | Hydrophosphoryl nucleophilic agents add to the CN bond of N-sulfonyltrichloroacetimidoylphosphonates to give unstable C,C-diphosphorylated adducts, which undergo competitive 1,2-C → N phosphorotropic rearrangement and dehydrochlorination with the formation of aza-Perkow reaction products, C,N-diphosphorylated dichlorovinylsulfonamides. This is the first reliably identified case of an aza-Perkow transformation for acid phosphites and their initial nucleophilic attack at the C atom of the azomethine bond in the aza-substrates. |
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Keywords: | N-Sulfonylimines Imidoylphosphonates Sulfonamides Diphosphonates Rearrangement Aza-Perkow reaction |
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