96349-58-5

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 67-66-3 chloroform 
• 2146-66-9 trichloromethyl lithium 
• 650-51-1 sodium trichloroacetate 
• 104-55-2 3-phenyl-propenal 
• 76-03-9 trichloroacetic acid 
• 5936-98-1 trichloromethyltrimethylsilane 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 351536-13-5 2-tert-butyldimethylsilyloxy-1,1,1-trichloro-4-phenyl-3-butene 
• 56-23-5 tetrachloromethane 

Downstream Products

• 351536-12-4 [(E)-1,1,1-trichloro-4-phenylbut-3-en-2-yloxy]trimethylsilane 
• 351536-13-5 2-tert-butyldimethylsilyloxy-1,1,1-trichloro-4-phenyl-3-butene 
• 1620143-55-6 ethyl 1,1,1-trichloro-4-phenylbut-3-en-2-yl carbonate 
• 937-58-6 (3E)-4-phenyl-3-buten-1-ol 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 1598391-95-7 dimethyl (2S,3R)-3-phenyl-2-((E)-3-phenylprop-1-en-1-yl)-pentanedioate 

Relevant academic research and scientific papers

1,4-Addition of TMSCCl3 to (E)-Fumaric Esters and Thermal Rearrangement of the Adducts to 3,4-Dichloropent-2-enedioates

The diesters (E)-RO2CCH=CHCO2R [R = Et, CH2Ph, iPr, iBu, tBu, 2-ethylhexyl, (-)-menthyl, (-)-bornyl] undergo 1,4-trichloromethylation with Me3SiCCl3 in 84-95% yield with Bu4NX (X = OAc, Cl,

Isothiourea-Catalyzed Enantioselective Functionalization of 2-Pyrrolyl Acetic Acid: Two-Step Synthesis of Stereodefined Dihydroindolizinones

Catalytic enantioselective functionalization of 2-pyrrolyl acetic acid with trichloromethyl enones using isothiourea catalysis is reported, leading to a range of stereodefined diesters and diamides after nucleophilic ring opening with either methanol or b

One-Carbon Homologation of Primary Alcohols and the Reductive Homologation of Aldehydes Involving a Jocic-Type Reaction

(Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope. The method is step-economical, and it nicely complements established one-carbon homologation strategies. (Trichloromethyl)carbinols, which are formed in one operation from either alcohols or aldehydes, can be converted into primary alcohols in a Jocic-type reaction involving LiBH4. The net result is a convenient two-step, one-carbon homologation of primary alcohols or a reductive one-carbon homologation of aldehydes featuring a broad substrate scope.

Decarboxylative trichloromethylation of aromatic aldehydes and its applications in continuous flow

Two new protocols for the efficient synthesis of 2,2,2- trichloromethylcarbinols, starting from aromatic aldehydes, have been developed. A combination of sodium trichloroacetate in the presence of malonic acid proved efficient for the transformation of el

Organocatalytic Michael addition-lactonisation of carboxylic acids using α,β-unsaturated trichloromethyl ketones as α,β-unsaturated ester equivalents

Isothiourea HBTM-2.1 catalyses the Michael addition-lactonisation of 2-aryl and 2-alkenylacetic acids and α,β-unsaturated trichloromethyl ketones. Ring-opening of the resulting dihydropyranones and subsequent alcoholysis of the CCl3 ketone with

β-(Carbonatoxy)alkyl radicals: A new subset of β-(ester)alkyl radical fragmentation during copper(I)-mediated synthesis of 1,1-dichloro-1-alkenes

A new subset of β-(ester)alkyl radicals is presented. It is the first study on the chemistry of β-(alkoxycarbonyloxy)alkyl radicals that fill the gap in the spectrum of the migrating groups in β-(ester)alkyl radical reactions. The change from less nucleofugal (acetate) group to the more nucleofugal (carbonate) group in the spectrum of the migrating group changed the reaction path from rearrangement to fragmentation. This approach has been used for the synthesis of 1,1-dichloroalkenes in high yields. The formation of dichloroalkenes was accounted by the involvement of alkene radical cation and carbonate anion pair (a CIP) as a result of heterolysis of the CO bond of the carbonate at the β-position of the β-(alkoxycarbonyloxy)alkyl radical. The alkene radical cation was trapped by nucleophilic reaction with MeOH to form methyl ester.

One-pot synthesis of trichloromethyl carbinols from primary alcohols

Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl3 followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.

Highly efficient asymmetric epoxidation of electron-deficient α,β-enones and related applications to organic synthesis

The asymmetric epoxidation of electrondeficient olefins has been achieved using inexpensive and readily available prolinols as catalysts with good to excellent yields and enantioselectivities. The utility of the resulting chiral epoxides was illustrated b

Copper(I)-promoted synthesis of chloromethyl ketones from trichloromethyl carbinols

(Chemical Equation Presented) Reaction of several trichloromethyl carbinols with 2 equiv of CuCl/bpy in refluxing DCE for 3 h afforded chloromethyl ketones in excellent yield by 1,2-H shift in the copper-chlorocarbenoid intermediate.

A versatile synthesis of 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes from trichloromethylcarbinols

CrCl2 converts trichloromethylcarbinols under mild conditions to (E)-α-haloalkylidene chromium carbenoids which add to aldehydes or are quenched with water affording 2-haloalk-2(Z)-en-1-ols and 1-chloro-1(Z)-alkenes, respectively, in high yield.