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Keywords:

  • cyclobutenes;
  • electrocyclic reactions;
  • silyl effect;
  • vinylallenes
Thumbnail image of graphical abstract

The kinetics and thermodynamics of the electrocyclization of vinylallenes are favorably influenced when a silyl substituent is introduced into the open-chain compound. A series of vinylallenes containing a silyl group at the vinyl terminus (1) gave good yields of the corresponding cyclobutenes 2 when heated at reflux in xylene. A theoretical explanation for this observation remains elusive.