Synthesis of unusual oxime ethers by reaction of tetranitromethane with B-alkylcatecholboranes

Chemistry. 2010 Sep 3;16(33):10171-7. doi: 10.1002/chem.201000680.

Abstract

The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers. A tentative mechanism is provided, which suggests the involvement of extremely fast addition of alkyl radicals to tetranitromethane. The substitution of one of the nitro groups in the oxime ethers by nucleophiles (such as secondary amines, halogens and styrene) and by radicals generated from B-alkylcatecholboranes is reported.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boranes / chemical synthesis
  • Boranes / chemistry*
  • Catechols / chemistry*
  • Ethers / chemical synthesis*
  • Molecular Structure
  • Oximes / chemical synthesis*
  • Stereoisomerism
  • Tetranitromethane / chemistry*

Substances

  • Boranes
  • Catechols
  • Ethers
  • Oximes
  • Tetranitromethane