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Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles

Publication ,  Journal Article
Padwa, A; Nara, S; Wang, Q
Published in: Tetrahedron Letters
January 23, 2006

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. © 2005 Elsevier Ltd. All rights reserved.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

January 23, 2006

Volume

47

Issue

4

Start / End Page

595 / 597

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Padwa, A., Nara, S., & Wang, Q. (2006). Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles. Tetrahedron Letters, 47(4), 595–597. https://doi.org/10.1016/j.tetlet.2005.11.026
Padwa, A., S. Nara, and Q. Wang. “Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles.” Tetrahedron Letters 47, no. 4 (January 23, 2006): 595–97. https://doi.org/10.1016/j.tetlet.2005.11.026.
Padwa A, Nara S, Wang Q. Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles. Tetrahedron Letters. 2006 Jan 23;47(4):595–7.
Padwa, A., et al. “Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles.” Tetrahedron Letters, vol. 47, no. 4, Jan. 2006, pp. 595–97. Scopus, doi:10.1016/j.tetlet.2005.11.026.
Padwa A, Nara S, Wang Q. Additive Pummerer reaction of heteroaromatic sulfilimines with carbon nucleophiles. Tetrahedron Letters. 2006 Jan 23;47(4):595–597.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

January 23, 2006

Volume

47

Issue

4

Start / End Page

595 / 597

Related Subject Headings

  • Organic Chemistry
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry