title: Allylic disulfide rearrangement and desulfurization: mild, electrophile-free thioether formation from thiols.
abstract: [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.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
authors.forename: David
authors.initials: D
authors.lastname: Crich
authors.forename: Franck
authors.initials: F
authors.lastname: Brebion
authors.forename: Venkataramanan
authors.initials: V
authors.lastname: Krishnamurthy
mesh_terms: 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
chemical_list: D004220:Disulfides; D010455:Peptides; D013438:Sulfhydryl Compounds; D013440:Sulfides