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Synthesis 1996; 1996(9): 1127-1130
DOI: 10.1055/s-1996-4334
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[(3-Dimethylamino)propyl]dimethylaluminum: A Convenient Reagent for Methylation and Ethynylation of Carbonyl Compounds

Wael Baidossi, Ayelet Rosenfeld, Brigit C. Wassermann, Stefan Schutte, Herbert Schumann1 , Jochanan Blum2
  • 1Institut für Anorganische und Analytische Chemie der Technischen Universität Berlin, Strasse des 17. Juni 135, D-10623 Berlin, Germany, Fax +49(30)76403268
  • 2Department of Organic Chemistry, Hebrew University, Jerusalem 91904, Israel, Fax +972(2)6513832
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Publication Date:
31 December 2000 (online)

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At 60-80°C the title compound methylates a variety of mono- and diketones. Aromatic aldehydes undergo simple methylation by the reagent only after initial treatment with an equivalent amount of AlCl3. Upon reaction of Me2Al(CH2)3NMe2 with terminal acetylenes the aluminum complex is converted into a carbonyl-alkynylation reagent.

dimethylaluminum complexes - methylation - alkynylation - carbonyl compounds