Schlotterbeck reaction

What is Schlotterbeck reaction?

The Schlotterbeck reaction, althougth first reported by Meyer in 1905, was named after Schlotterbeck. It involves the reaction between a carbonyl compound (aldehyde or ketone) and a diazoalkane, resulting in the formation of either a ketone or an oxirane (epoxide).

Schlotterbeck reaction - general reaction scheme
Schlotterbeck reaction

However, this reaction is not always straightforward, and the resulting product can vary. For instance, m– and p-nitrobenzaldehydes give acetophenones when reacted with diazomethane, while o-nitrobenzaldehyde produces o-nitrostyrene oxide.

As a result, the Schlotterbeck reaction is currently not widely used in organic synthesis, and alternative methods have been developed for the preparation of ketones. Nevertheless, this reaction remains valuable for the synthesis of β-keto esters using ethyl diazoacetate.

References

  • Meyer, H., Monatsh., 1905, 26, 1295
  • Schlotterbeck, F., Ber., 1907, 40B, 479
  • Schlotterbeck, F., Ber., 1907, 40B, 3000
  • Schlotterbeck, F., Ber., 1909, 42B, 2559
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