Stereochemistry of two new polyfunctionalized gem-dihalocyclopropanes

Acta Crystallogr C. 2002 Feb;58(Pt 2):o90-3. doi: 10.1107/s0108270101019680. Epub 2002 Jan 23.

Abstract

The two new gem-dihalogenocyclopropanes (1'S,3R)-3-(2',2'-dichloro-1'-methylcyclopropyl)-6-oxoheptanoic acid, C(11)H(16)Cl(2)O(3), (2), and (1'S,3R)-3-(2',2'-dibromo-1'-methylcyclopropyl)-6-oxoheptanoic acid, C(11)H(16)Br(2)O(3), (3), are isostructural. Both present two stereogenic centers at C1' and C3. The absolute configuration was determined by X-ray methods. The cyclopropyl rings are unsymmetrical, the shortest bond being distal with respect to the alkyl-substituted C atom.

MeSH terms

  • Crystallography, X-Ray
  • Cyclopropanes / chemical synthesis
  • Cyclopropanes / chemistry*
  • Heptanoic Acids / chemical synthesis
  • Heptanoic Acids / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Conformation
  • Pyrethrins / chemical synthesis
  • Pyrethrins / chemistry*

Substances

  • 3-(2',2'-dibromo-1-methylcyclopropyl)-6-oxoheptanoic acid
  • 3-(2',2'-dichloro-1'-methylcyclopropyl)-6-oxoheptanoic acid
  • Cyclopropanes
  • Heptanoic Acids
  • Pyrethrins