Boron trifluoride mediated addition of nucleophiles to endo- and exo-substituted norbornene derivatives


İŞLEYEN A., SAYRAÇ T., DOĞAN Ö.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, vol.59, no.1, pp.109-118, 2004 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 1
  • Publication Date: 2004
  • Title of Journal : ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
  • Page Numbers: pp.109-118

Abstract

Remote substituent effects on the regioselectivity and stereoselectivity in the boron trifluoride mediated addition of nucleophiles (iodide and bromide) to endo- and exo-2-substituted norbornene derivatives have been investigated. The main products of the reactions resulted from the regioselective addition of nucleophiles to the double bond of norbornene derivatives. Products resulting from the Wagner-Meerwein type rearrangement were also isolated in considerable amounts. All of the reactions gave the addition products in reasonably good yields with high regioselectivity. The endo/exo selectivity, on the other hand, changed depending on the nucleophile and the substrate.