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Zirconium(IV) chloride catalyzes the trans-hydrostannylation of acetylenes with Tri-n-butyltin hydride. It is used as a superior catalyst for the fries rearrangement of aryl acetates, giving the least hindered ortho-acetyl phenol in high yields at ambient temperatures. In the presence of ZrCl4, chloromethyl ethers are formed under mild conditions from acid chlorides and trioxane or paraformaldehyde.
Ch.Venkateshwar Reddy.; M Mahesh, P.V.K Raju.; T.Ramesh Babu.; V.V.Narayana Reddy. Zirconium(IV) chloride catalyzed one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones. Tetrahedron Letters. 2002, 43 (14), 2657-2659.
Harish K Patney.; Simon Margan. Zirconium(IV) chloride-silica catalysed thioacetalisation of carbonyl compounds. Tetrahedron Letters. 1996, 37 (26), 4621-4622.
Lewis acid. Promotes the rearrangement of hydroxy sulfones to ketones: J. Chem. Soc., Chem. Commun., 2289 (1994).
Catalyzes the trans-hydrostannylation of acetylenes with Tri-n-butyltin hydride, A13298: J. Chem. Soc., Chem. Commun., 2405 (1995); J. Org. Chem., 61, 4568 (1996). Allylstannanes also add trans-selectively to acetylenes under similar conditions: J. Chem. Soc., Chem. Commun., 1513 (1996).
Superior catalyst for the Fries rearrangement of aryl acetates, giving the least hindered ortho-acetyl phenol in high yields at ambient temperatures: Tetrahedron Lett., 37, 7659 (1996).
In the presence of ZrCl4, chloromethyl ethers are formed under mild conditions from acid chlorides and trioxane or paraformaldehyde: Tetrahedron Lett., 43, 6317 (2002).
Highly efficient and reusable catalyst for acetylation of phenols, thiols, amines and alcohols under solvent-free conditions, claimed to be superior to metal triflates: Synlett, 627 (2004).
For a brief feature on uses of this reagent in synthesis, see: Synlett, 1073 (2003).
Hazard Statements: H302-H314-H318
Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.