118171-45-2

Upstream product

• 53076-06-5 4,4-dichloro-1-phenyl-but-3-en-1-ol 
• 132277-01-1 (2,2-Dichloro-3-methyl-cyclopropyl)-diphenyl-methanol 
• 118171-44-1 2,2,2-trichloro-1-styrylethyl acetate 
• 115560-82-2 (E,Z)-(4,4,4-trichloro-but-1-enyl)-benzene 
• 14371-10-9 (E)-3-phenylpropenal 
• 300-57-2 allylbenzene 
• 866-23-9 diethyl (trichloromethyl)phosphonate 
• 90766-67-9 1,1-dibromo-4-phenyl-1,3-butadiene 
• 103639-68-5 3,4,4,4-tetrachloro-1-phenyl-butan-1-ol 
• 96349-58-5 (E)-1,1,1-trichloro-4-phenylbut-3-en-2-ol 
• 88108-59-2 1,1,1,3-tetrachloro-4-phenylbutane 

Downstream Products

• 2243-53-0 styrylacetic acid 
• 1256954-64-9 (2E,4E)-benzyl 2-chloro-5-phenylpenta-2,4-dienoate 
• 1256954-63-8 (2Z,4E)-benzyl 2-chloro-5-phenylpenta-2,4-dienoate 

Relevant academic research and scientific papers

A General Copper-Catalyzed Vinylic Halogen Exchange Reaction

An efficient and general system for the halogen exchange reaction in alkenyl halides has been developed. Upon reaction with catalytic amounts of copper iodide and trans-N,N′-dimethylcyclohexane-1,2-diamine in the presence of tetramethylammonium chloride or bromide, a wide range of easily accessible alkenyl iodides can be smoothly transformed to their far less available chlorinated and brominated derivatives in excellent yields and with full retention of the double bond geometry. This reaction also enables the chlorination of bromoalkenes and could be extended to the use of gem-dibromoalkenes.

Development of a general copper-catalyzed vinylic Finkelstein reaction—application to the synthesis of the C1–C9 fragment of laingolide B

An efficient and broadly applicable procedure for the copper-catalyzed vinylic Finkelstein reaction is reported. Using a simple, readily available and cheap catalytic system, a broad range of alkenyl iodides and bromides can be smoothly converted to their lower homologues with high yields and full retention of the double bond geometry. Key features of this vinylic Finkelstein reaction are its broad applicability, enabling the conversion of readily available alkenyl iodides to their less available brominated and chlorinated counterparts, and the mild reaction conditions compatible with a range of highly functionalized substrates. The potential of this vinylic halogen exchange reaction in total synthesis and medicinal chemistry was demonstrated by its successful use for the synthesis of the C1–C9 fragment of laingolide B and for the late-stage modification of drug-like molecules. The extension of this halogen exchange to the acetylenic and allenic Finkelstein reactions is also reported.

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.

Pd0-Catalyzed carbonylation of 1,1-dichloro-1-alkenes, a new selective access to Z-α-chloroacrylates

A novel and fully chemo- and stereoselective three component strategy leading to Z-α-chloroacrylates by a Pd0-catalyzed reaction of CO (1 atm) with 1,1-dichloro-1-alkenes and various alcohols is disclosed. This catalytic approach compares favourably with the Wittig type strategies as α-chloroacrylates of pure Z configuration are obtained in high yield. The Royal Society of Chemistry.

3,3,3-Trichloropropyl-1-triphenylphosphorane: A reagent for the synthesis of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes

,3,3,3-Trichloropropyl-1-triphenylphosphonium chloride is conveniently prepared from 2-chloroethanol, triphenylphosphine, and trichloroacetic acid. Deprotonation of this reagent generates 3,3,3-trichloropropyl-1-triphenylphosphorane, which reacts with aldehydes to give trichloromethylated (Z)-olefins, which are useful for the synthesis of (Z)-1,3-enynes, (Z,Z)-1-chloro-1,3-dienes, and 1,3-diynes in high yields and stereospecificities. Copyright

SmI2-mediated elimination reaction of trichloromethyl carbinols: A facile method to synthesize vinyl dichlorides

Samarium diiodide-mediated elimination reaction provides a simple and general method to synthesize vinyl dichlorides from trichloromethyl carbinols directly in good to excellent yields.

Reduction of trihalomethyl carbinols and their acetates, mesylates and tosylates by indium metal

A study of reduction of trihalomethyl carbinols and their derivatives by indium metal shows that while trichloromethyl carbinols produce a mixture of the corresponding dichloromethyl carbinol and vinylidene dichloride, the acetates, mesylates and tosylate

A new and practical synthesis of vinyl dichlorides via a non-Wittig-type approach

A practical approach for the conversion of aldehydes to vinyl dichlorides has been developed. These are three-step, one-pot reactions involving the formation of trichlorocarbinol by treatment of aldehydes with trichloroacetic acid and sodium trichloroacetate followed by in situ protection and elimination reactions to form the desired vinyl dichlorides in 85 to 95% yields. (C) 2000 Dupont Pharmaceuticals Company.

A novel synthesis of α- and β-halonaphthalenes via regioselective ring cleavage of aryl(gem-dihalocyclopropyl)methanols and its application to total synthesis of lignan lactones, justicidin e and taiwanin c

Acid treatment of two types of aryl(gem-dihalocyclopropyl)methanols (ADCM) 1 gave α- and β-halonaphthalenes in good yields with excellent selectivity. With the new method used as the key step, the two title natural lignan lactones were synthesized in seve

Reductive Addition of Polyhalomethanes and Their Related Compounds to Aldehydes and 1,2-Elimination of the Coupling Products in a Pb/Al Bimetal Redox System

A Pb/Al bimetal system was used to carry out reductive addition of tetrachloromethane, tetrabromomethane, bromotrichloromethane, trichloroacetamide, and trichloroacetonitrile to aldehydes.Subsequent 1,2-elimination of the halogen atom and hydroxyl group from the coupling products was also performed with the Pb/Al bimetal system.The technology was successfully applied to stereocontrolled syntheses of ethyl trans- and cis-3-(2,2-dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates.