Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles |
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Authors: | Albert Padwa Shinji Nara Qiu Wang |
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Institution: | Department of Chemistry, Emory University, Atlanta, GA 30322, USA |
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Abstract: | The additive Pummerer reaction of several heteroaromatic sulfilimines has been investigated. The overall process involves the reaction of the sulfilimine with TFAA to produce a transient N-tosyl-N-trifluoroacetyl sulfonium ion. Nucleophilic attack at the adjacent vinyl carbon results in the ejection of the sulfonamide group and the resulting thionium ion loses a proton to give the observed product. |
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