Arens–van Dorp synthesis

The Arens–van Dorp synthesis is a name reaction in organic chemistry.{{cite book |author=Daniel Zerong Wang |title=Comprehensive Organic Name Reactions and Reagents |version=1 |publisher=John Wiley & Sons, Inc. |date=2009 |isbn=978-0-471-70450-8 |pages=100–102}} It describes the addition of lithiated ethoxyacetylenes to ketones to give propargyl alcohols, which can undergo further reaction to form α,β-unsaturated aldehydes,{{cite journal |last1=Arens |first1=J. F. |last2=van Dorp |first2=D. A. |title=A new method for the synthesis of α,β-unsaturated aldehydes. Preparation of β-methylcinnamic aldehyde, citral and β-ionylidene acetaldehyde |journal=Recueil des Travaux Chimiques des Pays-Bas |date=1948 |volume=67 |issue=12 |pages=973–979 |doi=10.1002/recl.19480671206}} or esters.{{cite journal |last1=Rieder |first1=Curtis J. |last2=Winberg |first2=Karl J. |last3=West |first3=F. G. |title=Cyclization of Cross-Conjugated Trienes: The Vinylogous Nazarov Reaction |journal=Journal of the American Chemical Society |date=2009 |volume=131 |issue=22 |pages=7504–7505 |doi=10.1021/ja9023226|pmid=19435345 }} 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.{{cite book|editor-last1=Wang|editor-first1=Zerong|title=Comprehensive Organic Name Reactions and Reagents|chapter=Arens–Van Dorp Reaction (Isler Modification)|date=2009|publisher=Wiley-Interscience|location=Hoboken, NJ|isbn=9780471704508|edition=1st|doi=10.1002/9780470638859.conrr023}}{{cite journal|last1=Van Dorp|first1=D. A.|last2=Arens|first2=J. F.|title=Synthesis of Vitamin A Aldehyde-|journal=Nature|date=1947|volume=160|issue=4058|page=189|doi=10.1038/160189a0|pmid=20256189|bibcode=1947Natur.160..189V|doi-access=free}}

Image:RMV6 Arens-van Dorp Reaktion Isler Modifikation.svg