Synthesis of spiro[4.5]trienones by intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes

J Am Chem Soc. 2005 Sep 7;127(35):12230-1. doi: 10.1021/ja053079m.

Abstract

A wide variety of 3-halospiro[4.5]trienones are readily prepared in good to excellent yields by the intramolecular ipso-halocyclization of 4-(p-methoxyaryl)-1-alkynes under mild reaction conditions. ICl, I2, and Br2 are all effective electrophiles for this process under carefully optimized reaction conditions.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkynes / chemistry*
  • Anisoles / chemistry*
  • Cyclization
  • Hydrocarbons, Halogenated / chemistry
  • Models, Chemical
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*

Substances

  • Alkynes
  • Anisoles
  • Hydrocarbons, Halogenated
  • Spiro Compounds
  • anisole