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• 766-90-5 cis-1-phenyl-1-propylene 
• 87261-44-7 d,l-erythro-1-chloro-1-phenyl-2-iodopropane 
• 873-66-5 1-propenylbenzene 
• 64-19-7 acetic acid 
• 637-50-3 1-phenylpropene 
• 87261-47-0 threo-2-iodo-1-phenyl-1-propanol 

Relevant academic research and scientific papers

Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations

Vicinal dibromides and dichlorides are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that are traditionally synthesized using hazardous elemental chlorine and bromine. Meanwhile, the environmental persistence of halogenated pollutants necessitates improved approaches to accelerate their remediation. Here, we introduce an electrochemically assisted shuttle (e-shuttle) paradigm for the facile and scalable interconversion of alkenes and vicinal dihalides, a class of reactions that can be used both to synthesize useful dihalogenated molecules from simple alkenes and to recycle waste material through retro-dihalogenation. The reaction is demonstrated using 1,2-dibromoethane, as well as 1,1,1,2-tetrachloroethane or 1,2-dichloroethane, to dibrominate or dichlorinate, respectively, a wide range of alkenes in a simple setup with inexpensive graphite electrodes. Conversely, the hexachlorinated persistent pollutant lindane could be fully dechlorinated to benzene in soil samples using simple alkene acceptors.

Dichlorination of olefins with diphenyl sulfoxide/oxalyl chloride

The combination of diphenyl sulfoxide and oxalyl chloride was used to accomplish the dichlorination of olefins, in which chlorodiphenylsulfonium salt generated in situ was proposed to be the real active species as a chloronium ion source.

Electrocatalytic Radical Dichlorination of Alkenes with Nucleophilic Chlorine Sources

We report a Mn-catalyzed electrochemical dichlorination of alkenes with MgCl2 as the chlorine source. This method provides operationally simple, sustainable, and efficient access to a variety of vicinally dichlorinated compounds. In particular, alkenes with oxidatively labile functional groups, such as alcohols, aldehydes, sulfides, and amines, were transformed into the desired vicinal dichlorides with high chemoselectivity. Mechanistic data are consistent with metal-mediated Cl atom transfer as the predominant pathway enabling dual C-Cl bond formation and contradict an alternative pathway involving electrochemical evolution of chlorine gas followed by Cl2-mediated electrophilic dichlorination.

Vicinal dichlorination of olefins using NH4Cl and oxone

A mild and efficient protocol for the preparation of 1,2-dichloroalkane derivatives from olefins using NH4Cl and Oxone at room temperature is described. A variety of terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Moreover, 1,2-disubstituted symmetrical and unsymmetrical olefins dichlorinated with moderate to excellent diastereoselectivity. This method precludes the use of acidic additives and transition metals in the synthesis of vicinal dichlorides.

The α-halogenation of α,β-unsaturated carbonyls and dihalogenation of alkenes using bisacetoxyiodobenzene/pyridine hydrohalides

A procedure for the α-chlorination or bromination of a number of α,β-unsaturated carbonyls, and the dichlorination or bromination of alkenes, is developed using bisacetoxyiodobenzene (BAIB) and the HCl or HBr salt of pyridine. The reaction proceeds in an

Reaction of Benzeneseleninyl Chloride with Olefins in the Presence of a Lewis Acid. A Novel One Step Vinylic Chlorination

In the presence of aluminum chloride benzeneseleninyl chloride was found to be an exellent vinylic chlorinating reagent of olefins under mild conditions.However, such olefins as styrene, trans-stilbene, and trans-1-phenylpropene afforded dichloro adducts under similar conditions.A plausible reaction mechanism involving positive chlorine intermediate is proposed.

ROLE OF THE POLYMER BACKBONE ON THE REACTIVITY OF POLYMER-SUPPORTED (DICHLOROIODO)BENZENE

Chlorination of iodinated crosslinked polystyrene with Cl2 gave polyaryliododichloride containing 1.1 mmol of active chlorine per gram of resin, while fluorination of the same iodinated resin with XeF2 gave polyaryliododifluoride, co

BROMOCHLORINATION OF ALKENES WITH DICHLOROBROMATE(1 minus ) ION. II. REGIO- AND STEREOCHEMISTRY FOR THE BROMOCHLORINATION OF 1-PHENYLPROPENES WITH DICHLOROBROMATE(1 minus ) ION.

The bromochlorinations of 1-phenylpropenes with tetrabutylammonium dichlorobromate(1 minus ) in aprotic solvents (dielectric constants 5-36) were found to be completely anti stereospecific and nonregiospecific, although Markownikoff adduct was mainly form

Involvement of Neighboring Chlorine in the Exchange Reactions of Iodine Monochloride and Vicinal Organic Iodochlorides

The reaction of vicinal organic iodochlorides and ICl in CCl4 at 25 deg C forms vicinal organic dichlorides and iodine.The rate law for this exchange reaction of ICl and 2-chloro-3-iodo-2,3-dimethylbutane is overall third order: second order in ICl and first order in iodochloride with a value of k3 = 7.2 +/- 0.9 M-2s-1.Stereospecific exchange occurs in the reaction ICl and erythro- and threo-2-chloro-3-iodobutane.Thus the erythro isomer forms only meso-2,3-dichlorobutane while the threo isomers form only the dl dichloride.Nonstereospecific exchange occurs in the reaction of ICl and erythro- and threo-1-chloro-2-iodo-1-phenylpropane.The data support a mechanism involving a cationic intermediate.In addition, the chlorine atom is involved in the reaction prior to the product-determining step.