Silver-mediated allylic disulfide rearrangement for conjugation of thiols in protic media.
Alkyl and aryl allyl disulfides are induced to undergo the desulfurative allylic rearrangement by silver nitrate in protic solvents at room temperature, thereby removing the necessity for the use of phosphines as thiophilic reagents. The silver-mediated reaction functions at ambient temperature in protic solvents and in the absence of protecting groups.
Crich
David
D
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France. dcrich@icsn.cnrs-gif.fr
Subramanian
Venkataraman
V
Karatholuvhu
Maheswaran
M
D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D005978:Glutathione / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D010720:Phosphines / Q000737:chemistry; D011522:Protons; D012834:Silver / Q000737:chemistry*; D012835:Silver Nitrate / Q000737:chemistry; D012997:Solvents / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013696:Temperature
D000498:Allyl Compounds; D004220:Disulfides; D010720:Phosphines; D011522:Protons; D012997:Solvents; D013438:Sulfhydryl Compounds; D012834:Silver; C028009:diallyl disulfide; D012835:Silver Nitrate; D005978:Glutathione