Metal-catalyzed σ-bond rearrangement

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The metal-catalyzed σ-bond rearrangement is a collection of chemical reactions that occur with highly strained organic compounds are treated with metals like Ag+, Rh(I), or Pd(II) reagents.[1] [2+2] ring openings are sometimes observed:

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

These rearrangements proceed via oxidative addition of strained rings. Such processes are related to the activation of cyclopropanes by transition metals.

See also[edit]


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