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

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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 (US)
Pages (from-to)6433-6439
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number41
StatePublished - Nov 8 2020

Bibliographical note

Funding Information:
This work was supported by a research grants from the Russian Science Foundation (RSF‐16‐13‐10081‐P) and the National Science Foundation (CHE‐1759798). A. S. is thankful to JSPS Fund for the Promotion of Joint International Research (Grant No 16KK0199) and JST CREST (No. JRMJCR19R2). Some research was carried out using the core facilities of TPU's “Physical and chemical methods of analysis”.


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


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