4412-45-7

Upstream product

• 622-97-9 1-ethenyl-4-methylbenzene 
• 1866-39-3 trans-p-methylcinnamic acid 
• 87-90-1 trichloroisocyanuric acid 
• 156-60-5 trans-1,2-dichloroethylene 
• 195062-57-8 p-tolylboronic pinacol ester 
• 104-87-0 4-methyl-benzaldehyde 
• 103721-99-9 (4R,5R)-4-Chloro-5-p-tolyl-[1,3]oxathiolane 3,3-dioxide 
• 93746-79-3 3-chloro-3-(p-methylbenzyl)diazirine 
• 691-38-3 (Z)-4-methyl-2-pentene 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 1866-39-3 4-methylcinnamic acid 
• 127-65-1 chloroamine-T 
• 106-49-0 p-toluidine 

Downstream Products

• 132725-78-1 7-methyl-2-(4-methylphenyl)naphthalene 
• 4412-45-7 trans-p-methyl-β-chlorostyrene 
• 1595-05-7 p-butyltoluene 
• 54948-51-5 1,4-di-(4'-methylphenyl)-buta-1,3-diene 
• 7568-23-2 1,4-di-p-tolylbutane 
• 54372-77-9 (E)-1-(but-1-en-1-yl)-4-methylbenzene 

Relevant academic research and scientific papers

Transition metal free large-scale synthesis of aromatic vinyl chlorides from aromatic vinyl carboxylic acids using bleach

While continuing our research on Hunsdiecker reaction, we came across an interesting application of bleach, sodium hypochlorite (NaOCl) for decarboxylative chlorination reaction. The reaction is easily scaled up to 10 mmol. The reaction has good tolerance towards wide variety of functional groups. The reaction has mild conditions and gave relatively high chemical yield of the desired product.

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.

Highly regio- and diastereoselective halohydroxylation of olefins: A facile synthesis of vicinal halohydrins

An efficient method for the synthesis of vicinal chlorohydrin or bromohydrin derivatives has been developed on the basis of direct halohydroxylation of various olefins with electrondonating or withdrawing substituent. The reactions were carried out under mild conditions in the presence of N-tosyl-l-threonine (NTsLT) as an acidic additive using chloramine T trihydrate, 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) or N-bromoacetamide (AcNHBr) as the halogen source, respectively, affording the corresponding vicinal halohydrins in good to high yields with excellent regio- and stereoselectivities.

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.

INVESTIGATIONS ON REACTIONS OF CHLORINE DIOXIDE AND SODIUM CHLORITE WITH ORGANIC COMPOUNDS. PART XXXV. REACTIONS OF CHLORINE DIOXIDE WITH RING-SUBSTITUTED STYRENES

Reactions of chlorine dioxide with ring substituted styrenes (1a-n) in carbon tetrachloride at 52-54 deg C were studied.The reaction products were isolated and characterised.It has been found that methyl-, chloro-, nitrostyrenes and 4-methoxystyrene are attacked by chlorine dioxide exclusively on the vinyl group, to yield the corresponding α-chloroacetophenones (2), diastereoisomers of β-chlorostyrene (6,7), oxidation products (8,9) and some polymers.Oxidation of its phenolic hydroxyl groups and vinyl polymerization took place in hydroxystyrenes.

Substituent and Temperature Effects on the Reactions of Benzylchlorocarbene with Alcohol

The insertion reaction of the para-substituted benzylchlorocarbenes with methanol shows a second-order dependence in methanol, but only a first-order dependence in ethylene glycol.The results are consistent with a mechanism whereby the carbene inserts into the O-H bond of the alcohol dimer or oligomer by electrophilic attack of the carbene on the oxigenone pair to produce a reversibly formed ylide intermediate.The effects of the substituents indicate that electron-releasing group favours rearrangement while electron-withdrawing group facilitates insertion.Photolysis of halogenodiazirines in methanol at low temperatures give rise to V-shaped Arrhenius behaviour and the importance of N2 in influencing the reactivity of the singlet halogenocarbene in the matrix is demonstrated.