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  • Imino‐λ 3 ‐iodane and Catalytic Amount of I 2 ‐Mediated Synthesis of N ‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement
Title: Imino‐λ 3 ‐iodane and Catalytic Amount of I 2 ‐Mediated Synthesis of N ‐Allylsulfenamides via [2,3]‐Sigmatropic Rearrangement
A facile metal‐free [2,3]‐sigmatropic rearrangement reaction of allyl sulfides viaN‐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 correspondingN‐allylsulfenamide compounds in moderate to good yields. SeveralN‐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 ofN‐sulfilimine species, followed by [2,3]‐sigmatropic rearrangement to form theN‐allylsulfenamide.  more » « less
Award ID(s):
1759798
PAR ID:
10238586
Author(s) / Creator(s):
 ;  ;  ;  ;  ;  ;  ;  
Publisher / Repository:
Wiley Blackwell (John Wiley & Sons)
Date Published:
Journal Name:
European Journal of Organic Chemistry
Volume:
2020
Issue:
41
ISSN:
1434-193X
Format(s):
Medium: X Size: p. 6433-6439
Size(s):
p. 6433-6439
Sponsoring Org:
National Science Foundation
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