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3-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, aliphatic aldehydes undergo the acyloin condensation in the presence of this catalyst and mild base. It acts as a catalyst for the addition of aliphatic and heterocyclic aldehydes to α,β-unsaturated ketones, nitriles and esters.
Aliphatic aldehydes undergo the acyloin condensation in the presence of this catalyst and mild base. For example (butyraldehyde to butyroin), see: Org. Synth. Coll., 7, 95 (1990).
The same system is effective in catalyzing the addition of aldehydes to electron-deficient alkenes, including ɑß-unsaturated ketones, esters and nitriles (Stetter reaction), providing a non-toxic alternative to cyanide in these reactions; e.g. in the synthesis of dihydrojasmone: Org. Synth. Coll., 8, 620 (1993):
For reviews, see: Angew. Chem. Int. Ed., 15, 639 (1976); Org. React., 40, 407 (1991). For a further example, see Phenyl vinyl sulfone, A14794.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.