ChemInform Abstract: Allyl Sulfide Synthesis of Phenylthio Migration: Relationship Between Stereochemistry of Starting Materials and Regioselectivity of Double Bond Formation.
Abstract
Reduction of the phenylthio ketone (I) affords the syn- and anti-phenylthio alcohols (II) and (III).
ChemInform Abstract
Reduction of the phenylthio ketone (I) affords the syn- and anti-phenylthio alcohols (II) and (III). Phenylthio migration of each isomer preferentially leads to one of the two regioisomeric allylic sulfides (IV) and (V). Other examples are given; the regioselectivities of double bond formation and the E/Z selectivities of the formed allylic sulfides are affected by the substituents.