18684-80-5

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 563-79-1 2,3-Dimethyl-2-butene 
• 93746-79-3 3-chloro-3-(p-methylbenzyl)diazirine 
• 691-38-3 (Z)-4-methyl-2-pentene 
• 1866-39-3 trans-p-methylcinnamic acid 
• 156-60-5 trans-1,2-dichloroethylene 
• 195062-57-8 p-tolylboronic pinacol ester 
• 67-56-1 methanol 
• 103721-99-9 (4R,5R)-4-Chloro-5-p-tolyl-[1,3]oxathiolane 3,3-dioxide 
• 4412-45-7 1-(2-chlorovinyl)-4-methylbenzene 
• 104-87-0 4-methyl-benzaldehyde 
• 87-90-1 trichloroisocyanuric acid 
• 64-17-5 ethanol 

Downstream Products

• 54948-51-5 1,4-di-(4'-methylphenyl)-buta-1,3-diene 
• 54372-77-9 (E)-1-(but-1-en-1-yl)-4-methylbenzene 
• 1595-05-7 p-butyltoluene 
• 7568-23-2 1,4-di-p-tolylbutane 

Relevant academic research and scientific papers

Continuous Flow Chlorination of Alkenyl Iodides Promoted by Copper Tubing

A simple continuous flow synthesis of alkenyl chlorides from the corresponding readily available alkenyl iodides in copper reactor tubing is described. A variety of alkenyl chlorides were obtained in good to excellent yields with full retention of the dou

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.

Rhodium-catalyzed cross-coupling of alkenyl halides with arylboron compounds

The rhodium(I)-catalyzed reaction between arylboronic esters and excess 1,2-dichloroethene selectively afforded (2-chlorovinyl)arenes. Double arylation yielding 1,2-diarylethenes was observed when 1,2-dibromoethene was reacted with 2.5 equivalents of aryl

A green hunsdiecker reaction of cinnamic acids

Tribromo- and trichloroisocyanuric acids react with cinnamic acids in NaOH/H2O/Et2O at room temperature to produce (E)-2-halostyrenes regioselectively in 25-95percent yield. Mechanism studies using Hammett correlations and DFT (density functional theory) calculations have shown that this reaction has as rate determining step the electrophilic addition of chlorine atom to the double bond.

π-extended conjugate phenylacetylenes. Synthesis of 4-[(E) and (Z)-2-(4-ethenylphenyl)ethenyl]pyridine. Dimerization, quaternation and formation of charge-transfer complexes

The conjugate (E)- and (Z)-(4′-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4′-pyridylethenyl-4-phenyl-β-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4′-pyridylethenyl)-4-phenyl]-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono- and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD.

Halodecarboxylation of a,β-unsaturated carboxylic acids bearing aryl and styrenyl group at β-carbon with Oxone and sodium halide

Reaction of α,β-unsaturated carboxylic acid bearing aryl and styrenyl group at β-carbon with Oxone and sodium halide in aqueous acetonitrile afforded the corresponding haloalkenes.

Stereoselective synthesis of (E)-β-arylvinyl halides by microwave-induced Hunsdiecker reaction

(E)-β-Arylvinyl halides were prepared in high yields in a short reaction (1-2 min) by microwave irradiation of the corresponding 3-arylpropenoic acids in the presence of N-halosuccinimide and catalytic LiOAc.

Oxidative Halo-Decarboxylation of α,β-Unsaturated Carboxylic Acids

A procedure for oxidative halo-decarboxylation of α,β-unsaturated carboxylic acids using iodosylbenzene, or iodosylbenzene diacetate, and N-chloro-, N-bromo-, or N-iodosuccinimide is presented.Good yields of the corresponding bromoalkenes are obtained when the α,β-unsaturated carboxylic acids are substituted with an aromatic substituent in the β-position and N-bromosuccinimide is used as the halogenation reagent.The scope of mainly the oxidative bromo-decarboxylation reaction is presented, and a tentative mechanism is proposed.

Thermolysis and Photolysis of 3-Chloro-3-benzyldiazirines in Alkenes: Evidence for a Carbene-Alkene Complex

Photolysis and thermolysis of substituted 3-chloro-3-benzyldiazirines in alkenes yielded cyclopropanes and chlorostyrenes as products.The results suggest that the cyclopropanation of benzylchlorocarbenes is independent of substituents.However, 1,2-hydrogen migration is accelerated by OCH3 or CH3 substituents, and is decelerated by a Cl substituent on the phenyl ring.These results support the existence of an energy barrier to 1,2-H migration.Evidence is provided for carbene-alkene complexation.