Ylide-Functionalization via Metalated Ylides: Synthesis and Structural Properties.

ABSTRACT: The α-metallated ylides [Ph₃P-C-Z]^-M⁺ (with Z=SO₂Tol or CN and M=Na or K) were used as versatile nucleophiles for the facile access to ylide-substituted compounds. Halogenations, alkylations, carbonylations and functionalization reactions with main group element halides were easily accomplished by simple trapping reactions with the appropriate electrophiles. X-ray crystallographic studies of all compounds - including the first structures of α-fluorinated P-ylides - showed remarkable differences in the ylide backbone depending on the substituents. In the fluorinated compounds, a change from a fully planar to a pyramidalized ylidic carbon centre was observed despite the strongly anion-stabilizing ability of the yldiide substituent. π-Donation from

SUBMITTER: Schwarz C 

PROVIDER: S-EPMC6519319 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature