Phosphonium-iodonium ylides with heteroatomic groups in the synthesis of annelated P-containing heterocycles

J Org Chem. 2013 Dec 6;78(23):11691-7. doi: 10.1021/jo401514d. Epub 2013 Nov 18.

Abstract

The preparation and chemistry of novel sulfonyl- and phosphoryl-derived λ(3)-iodanes are reported. These compounds with three different heteroatoms attached to a negatively charged C atom represent potentially useful reagents that combine in one molecule the synthetic advantages of a phosphonium ylide and an iodonium salt. Specifically, they can react with a number of acetylenes, leading to hitherto unknown sulfonyl- and phosphoryl-substituted phosphinolines, phosphininothiophenes, and a novel type of annelated P-containing heterocycle--phosphininopyrazole.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / chemistry
  • Hydrocarbons, Iodinated / chemistry*
  • Molecular Structure
  • Organophosphonates / chemistry*

Substances

  • Heterocyclic Compounds
  • Hydrocarbons, Iodinated
  • Organophosphonates