54034-90-1

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 5936-98-1 trichloromethyltrimethylsilane 
• 100-52-7 benzaldehyde 
• 56-23-5 tetrachloromethane 
• 25436-07-1 trimethylsilyl trichloroacetate 

Downstream Products

• 2000-43-3 2,2,2-trichloro-1-phenylethanol 
• 80423-31-0 (Z)-2-chloro-1-phenyl-1-(trimethylsilyloxy)ethylene 

Relevant academic research and scientific papers

EINTOPFSYNTHESE TRICHLOROMETHYLSUBSTITUIERTER ALKOHOLE

A new one-pot synthesis of alcohols RCH(OH)CCl3 starting from CCl4, Me3SiCl, Mg and aldehydes RCHO is described.

1,2-H shift in copper-chlorocarbenoid intermediate during CuCl/bpy-promoted stereoselective dechlorination of 2,2,2-trichloroethyl alkyl ethers to (Z)-1-alkoxy-2-chloroethenes

(Chemical Equation Presented) Reaction of 2,2,2-trichloroethyl alkyl ethers with 2 molar equiv of CuCl/bpy in refluxing DCE yielded (Z)-1-alkoxy-2- chloroethenes stereoselectively as the major product via 1,2-H shift in copper-chlorocarbenoid intermediate. 2,2,2-Trichloroethyl carboxylates undergo a radical 1,2-acyloxy shift under similar conditions.

Trichloromethyltrimethylsilane, sodium formate, and dimethylformamide: A mild, efficient, and general method for the preparation of trimethylsilyl- protected 2,2,2-trichloromethylcarbinols from aldehydes and ketones

(Chemical Equation Presented) New conditions for the preparation of trimethylsilyl-protected 2,2,2-trichloromethylcarbinols 2 from aldehydes and ketones are reported. Compounds 2, which are important intermediates in organic synthesis, were obtained in excellent yields by use of a combination of trichloromethyltrimethylsilane (TMSCCI3), and a catalytic amount of sodium formate (HCOONa) in dimethylformamide (DMF). Substrates bearing highly sensitive protecting groups have been successfully subjected to our conditions. We also describe a one-pot procedure that gives direct access to 2,2,2-trichloromethylcarbinols 3. This methodology avoids the use of strong bases usually required for the synthesis of 3 (Wyvratt et al. J. Org. Chem. 1987, 52, 944; Aggarwal and Mereu, J. Org. Chem. 2000, 65, 7211).

TRICHLOROMETHYL ANION CHEMISTRY FROM TRIMETHYLSILYL TRICHLOROACETATE

The reaction of trimethylsilyl trichloroacetate with aldehydes and ketones in the presence of fluoride ion gives the trichloromethyl adducts.With potassium fluoride the reaction with cyclohexenone and crotonaldehyde results in clear 1,2 addition.

Dichlorocarbene from Flash Vacuum Pyrolysis of Trimethyl(trichloromethyl)silane. Possible Observation of 1,1-Dichloro-3-Phenyl Carbonyl Ylide

Flash vacuum pyrolysis of trimethyl(trichloromethyl)silane 3 at 500-700 deg C was shown to be a simple and efficient method for the production of :CCl2 in the gas phase.The copyrolysis of silane 3 and benzaldehyde (7) at 600 deg C led to 1,1,1-trichloro-2-phenyl-2-(trimethylsiloxy)ethane (8), a 1:1 adduct, in addition to benzal chloride (15) and α-chlorophenylacetyl chloride (16), product thought to arise from 1,1-dichloro-3-phenyl carbonyl ylide 17 as outlined in Scheme I.An orange-red material trapped at deg K could be photobleached as well as thermally bleached and had an IR band at 1650 cm-1 and a si gnificant absorption with λmax 510 nm (and a broad shoulder at a 580 nm).

TRIMETHYLSILYL TRICHLOROACETATE: A NEW REAGENT FOR SALT-FREE SILYLATIONS

Trimethylsylil trichloroacetate (1) is a convenient reagent for the silylation of phenols, carboxylic acids, mercaptans, amides, acetylenes, and β-keto esters, while the reaction of 1 with aldehydes and ketones affords silylated trichloromethyl carbinols (5).