130837-17-1Relevant articles and documents
METALATION REACTIONS. PART XVII. DILITHIATION OF PHENYL ISOPROPYL SULPHONE
Cabiddu, Maria G.,Cabiddu, Salvatore,Fattuoni, Claudia,Floris, Costantino,Gelli, Gioanna,Melis, Stefana
, p. 139 - 144 (2007/10/02)
The general utility of dimetalation reactions of phenyl iso-propyl sulphone for the preparation of ortho,alpha-substituted aryl sulphones is described.All the products were obtained in satisfactory yields. Key words: Alkyl aryl sulphones; metalation; poly
Scope and limitations in the use of α-silyl and α-stannyl sulfones as latent α-sulfonyl anions
Lamothe,Anderson,Fuchs
, p. 1675 - 1693 (2007/10/02)
Three methods for the regeneration of α-sulfonyl anions from α-silyl sulfones and α-stannyl sulfones are investigated. These methods include: (1) treatment of α-silyl sulfones with electrophiles (aldehydes and acid halides) in the presence of fluoride ion; (2) reaction of α-silyl sulfones with n-butyllithium which produces an α-silyl anion via a migration of the -SiMe3 group from the α-position to the ortho-position of the phenyl sulfones; and (3) direct transmetalation of α-stannyl sulfone by treatment with n-butyllithium. The addition of cerium [III] chloride is shown to substantially decrease enolization problems associated with addition of α-sulfonyl anions to carbonyl compounds bearing enolizable protons.