Imino-λ3-iodane and Catalytic Amount of I2-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement

Cody L. Makitalo, Akira Yoshimura, Gregory T. Rohde, Irina A. Mironova, Rosa Y. Yusubova, Mekhman S. Yusubov, Viktor V. Zhdankin, Akio Saito

Research output: Contribution to journalArticlepeer-review


A facile metal-free [2,3]-sigmatropic rearrangement reaction of allyl sulfides via N-sulfilimine intermediates has been developed. Treatment of allyl sulfides with imino-λ3-iodanes in the presence of a catalytic amount of elemental iodine allowed the reaction to proceed under mild conditions and gave the corresponding N-allylsulfenamide compounds in moderate to good yields. Several N-allylsulfenamide structures have been confirmed by single-crystal X-ray crystallography. The reaction initially involves the sulfonylimino group transfer reaction between imino-λ3-iodane and the sulfur atom, resulting in the formation of N-sulfilimine species, followed by [2,3]-sigmatropic rearrangement to form the N-allylsulfenamide.

Original languageEnglish
Pages (from-to)6433-6439
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number41
Publication statusPublished - 8 Nov 2020


  • Hypervalent compounds
  • Iodine
  • Sigmatropic rearrangement
  • Sulfilimines
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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