title: Arylthio-metal exchange of α-arylthioalkanenitriles.
abstract: The addition of BuLi, Bu3MgLi, Et2ZnBuLi, or Me2CuLi to α-arylthioalkanenitriles triggers an arylthio-metal exchange. NMR spectroscopic analyses implicate organometallic attack on sulfur forming a three-coordinate sulfidate as the key intermediate. Electrophilic trapping affords tertiary and quaternary nitriles in high yield. The method addresses the challenge of improving the functional group tolerance and preventing polyalkylations.
authors: Department of Chemistry & Biochemistry, Duquesne University , Pittsburgh, Pennsylvania 15282-1530, United States.
authors: Dinesh
authors: D
authors: Nath
authors: Melanie C
authors: MC
authors: Skilbeck
authors: Iain
authors: I
authors: Coldham
authors: Fraser F
authors: FF
authors: Fleming