Arens–van Dorp synthesis

The Arens–van Dorp synthesis is a name reaction in organic chemistry.^[1] It describes the addition of lithiated ethoxyacetylenes to ketones to give propargyl alcohols, which can undergo further reaction to form α,β-unsaturated aldehydes,^[2] or esters.^[3] There is also a variation of this reaction called the Isler modification, where the acetylide anion is generated in situ from β-chlorovinyl ether using lithium amide.^[4][5]

The Isler modification

References

1. Daniel Zerong Wang (2009). Comprehensive Organic Name Reactions and Reagents. 1. John Wiley & Sons, Inc. pp. 100–102. ISBN 978-0-471-70450-8.
2. Arens, J. F.; van Dorp, D. A. (1948). "A new method for the synthesis of α,β-unsaturated aldehydes. Preparation of β-methylcinnamic aldehyde, citral and β-ionylidene acetaldehyde". Recueil des Travaux Chimiques des Pays-Bas. 67 (12): 973–979. doi:10.1002/recl.19480671206.
3. Rieder, Curtis J.; Winberg, Karl J.; West, F. G. (2009). "Cyclization of Cross-Conjugated Trienes: The Vinylogous Nazarov Reaction". Journal of the American Chemical Society. 131 (22): 7504–7505. doi:10.1021/ja9023226. PMID 19435345.
4. Wang, Zerong, ed. (2009). "Arens–Van Dorp Reaction (Isler Modification)". Comprehensive Organic Name Reactions and Reagents (1st ed.). Hoboken, NJ: Wiley-Interscience. doi:10.1002/9780470638859.conrr023. ISBN 9780471704508.
5. Van Dorp, D. A.; Arens, J. F. (1947). "Synthesis of Vitamin A Aldehyde-". Nature. 160 (4058): 189. Bibcode:1947Natur.160..189V. doi:10.1038/160189a0. PMID 20256189.