Allylic disulfide rearrangement and desulfurization: mild, electrophile-free thioether formation from thiols.
[reaction: see text] Secondary and tertiary allylic 2-pyridyl and 2-benzothiazolyl disulfides react with thiol groups at room temperature to give secondary and tertiary allyl alkyl disulfides. On the addition of a phosphine, a desulfurative sigmatropic rearrangement takes place at room temperature to give thioethers.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Brebion
Franck
F
Krishnamurthy
Venkataramanan
V
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004220:Disulfides / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013440:Sulfides / Q000138:chemical synthesis* / Q000737:chemistry
D004220:Disulfides; D010455:Peptides; D013438:Sulfhydryl Compounds; D013440:Sulfides