Reaction of unstabilized iodonium ylides with organoboranes

Org Lett. 2004 Apr 29;6(9):1505-8. doi: 10.1021/ol0495669.

Abstract

[reaction: see text] Exposure of monocarbonyl iodonium ylides, generated by the ester exchange of (Z)-(2-acetoxyvinyl)-lambda(3)-iodanes with EtOLi, to organoboranes results in a 1,2-shift of a carbon ligand from boron to the ylide carbons, which probably generates hitherto uncharacterized alpha-boryl ketones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemistry*
  • Hydrocarbons, Iodinated / chemical synthesis
  • Hydrocarbons, Iodinated / chemistry*
  • Molecular Structure
  • Onium Compounds / chemical synthesis*
  • Onium Compounds / chemistry*

Substances

  • Boranes
  • Hydrocarbons, Iodinated
  • Onium Compounds