Dieckmann condensation

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Dieckmann condensation
Named after Walter Dieckmann
Reaction type Ring forming reaction
Identifiers
Organic Chemistry Portal dieckmann-condensation
RSC ontology ID RXNO:0000065

The Dieckmann condensation is the

intermolecular reaction is the Claisen condensation. Dieckmann condensations are highly effective routes to 5-, 6-, and 7-member rings, but poor for larger rings.[4]

The Dieckmann condensation
The Dieckmann condensation

Reaction mechanism

Deprotonation of an ester at the α-position generates an

Brønsted-Lowry acid (H3O+ for example) re-forms the β-keto ester.[5]

Dieckmann condensation reaction mechanism for the example given
Dieckmann condensation reaction mechanism for the example given

Due to the steric stability of five- and six-membered rings, these structures will preferentially be formed. 1,6 diesters will form five-membered cyclic β-keto esters, while 1,7 diesters will form six-membered β-keto esters.[6]

Animation zum Reaktionsmechanismus der Dieckmann-Kondensation
Animation of the reaction mechanism

Further reading

  • Dieckmann, W. Ber. 1894, 27, 102 & 965
  • Dieckmann, W. Ber. 1900, 33, 595 & 2670
  • Dieckmann, W. Ann. 1901, 317, 51 & 93

See also

References

  1. ^ Davis, B. R.; Garrett, P. J. Compr. Org. Synth. 1991, 2, 806-829. (Review)
  2. ISBN 9780470771099
    .
  3. ISBN 0471264180
    .
  4. ISBN 978-0-471-72091-1
  5. ISBN 978-0073327495
    .
  6. ^ "Dieckmann Condensation". Organic Chemistry Portal.
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