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- Title
Imino-λ³-iodane and Catalytic Amount of I<sub>2</sub>-Mediated Synthesis of N-Allylsulfenamides via [2,3]-Sigmatropic Rearrangement.
- Authors
Makitalo, Cody L.; Yoshimura, Akira; Rohde, Gregory T.; Mironova, Irina A.; Yusubova, Rosa Y.; Yusubov, Mekhman S.; Zhdankin, Viktor V.; Saito, Akio
- Abstract
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.
- Subjects
SIGMATROPIC rearrangements; REARRANGEMENTS (Chemistry); X-ray crystallography; SULFUR; SULFIDES; IODINE
- Publication
European Journal of Organic Chemistry, 2020, Vol 2020, Issue 41, p6433
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202000961