Di-π-methane Rearrangement

Di-π-methane Rearrangement

Overall Score3.5
  • Generality
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  • General Characteristics

1,4-Dienes undergo light-promoted rearrangement to give vinylcyclopropanes. The scope of this reaction includes dienes containing heteroatoms such as oxygen and nitrogen and even certain benzene ring skeletons.

  • General References

<photochemical reactions in total synthesis>

  • Reaction Mechanism


  • Examples

An example of oxa-di-π-methane rearrangement.[1]


The synthesis of modhephene utilizing oxa-di-π-methane rearrangement.[2]


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  • References

[1] Givens, R. S.; Oettle, W. F.; Coffin, R. L.; Carlson, R. G. J. Am. Chem. Soc. 1971, 93, 3957. DOI: 10.1021/ja00745a024
[2] Mehta, G.; Subrahmanyam, D. J. Chem. Soc. Chem. Commun. 1985, 768. DOI: 10.1039/C39850000768

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