Metal-ion-catalyzed σ-bond rearrangement

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The metal-ion-catalyzed σ-bond rearrangement reaction occurs with highly saturated organic ring molecules treated by Ag+, Rh(I), or Pd(II) ions.[1] Two types of the reaction were noted: [2+2] ring openings, and a conversion to another ring system:

Scheme 1. Metal-ion-catalyzed σ-bond rearrangement

A mechanism for this rearrangement reaction is not completely understood, however some explanations were suggested.

See also[edit]


  1. ^ Michael B. Smith, Jerry March, March's Advanced Organic Chemistry, 5 th Ed., John Wiley & Sons, Inc., 2001, p. 1459. ISBN 0-471-58589-0