5216-32-0

Usage

InChI:InChI=1/C16H14ClNO2/c1-2-15(19)13-10-12(17)8-9-14(13)18-16(20)11-6-4-3-5-7-11/h3-10H,2H2,1H3,(H,18,20)

Upstream product

• 676-58-4 methylmagnesium chloride 
• 98-07-7 Benzotrichlorid 
• 501-65-5 diphenyl acetylene 
• 13700-81-7 1,1,2,2-tetrachloro-1,2-diphenylethane 
• 100-42-5 styrene 
• 98-87-3 benzylidene dichloride 
• 1073-67-2 4-vinylbenzyl chloride 
• 637-69-4 4-Methoxystyrene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 2039-86-3 3-bromostyrene 
• 700-60-7 trichlorovinylbenzene 
• 100-34-5 benzene diazonium chloride 
• 72791-55-0 trichloro[Te(Z)-2-chloro-1,2-diphenylvinyl]tellurium(IV) 
• 108-24-7 acetic anhydride 

Downstream Products

• 501-65-5 diphenyl acetylene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 

Relevant academic research and scientific papers

Electrolysis of trichloromethylated organic compounds under aerobic conditions catalyzed by the B12 model complex for ester and amide formation

The electrolysis of benzotrichloride at -0.9 V vs. Ag/AgCl in the presence of the B12 model complex, heptamethyl cobyrinate perchlorate, in ethanol under aerobic conditions using an undivided cell equipped with a platinum mesh cathode and a zinc plate anode produced ethylbenzoate in 56% yield with 92% selectivity. The corresponding esters were obtained when the electrolysis was carried out in various alcohols such as methanol, n-propanol, and i-propanol. Benzoyl chloride was detected by GC-MS during the electrolysis as an intermediate for the ester formation. When the electrolysis was carried out under anaerobic conditions, partially dechlorinated products, 1,1,2,2-tetrachloro-1,2-diphenylethane and 1,2-dichlorostilibenes (E and Z forms), were obtained instead of an ester. ESR spin-trapping experiments using 5,5,-dimethylpyrroline N-oxide (DMPO) revealed that the corresponding oxygen-centered radical and carbon-centered radical were steadily generated during the electrolyses under aerobic and anaerobic conditions, respectively. Applications of the aerobic electrolysis to various organic halides, such as substituted benzotrichlorides, are described. Furthermore, the formation of amides with moderate yields by the aerobic electrolysis of benzotrichloride catalyzed by the B12 model complex in the presence of amines in acetonitrile is reported.

Oxygen-Controlled Catalysis by Vitamin B12-TiO2: Formation of Esters and Amides from Trichlorinated Organic Compounds by Photoirradiation

An oxygen switch in catalysis of the cobalamin derivative (B12)-TiO2 hybrid catalyst for the dechlorination of trichlorinated organic compounds has been developed. The covalently bound B12 on the TiO2 surface transformed trichlorinated organic compounds into an ester and amide by UV light irradiation under mild conditions (in air at room temperature), while dichlorostilbenes (E and Z forms) were formed in nitrogen from benzotrichloride. A benzoyl chloride was formed as an intermediate of the ester and amide, which was detected by GC-MS. The substrate scope of the synthetic strategy is demonstrated with a range of various trichlorinated organic compounds. A photo-duet reaction utilizing the hole and conduction band electron of TiO2 in B12-TiO2 for the amide formation was also developed.

Chromium-carbyne complexes: Intermediates for organic synthesis

(Chemical Equation Presented) On the same route: Chromium-carbyne complexes are readily prepared by treatment of 1,1,1-trichloromethyl reagents with chromium(II) chloride. They serve as intermediates in the selective formation of a wide variety of products, such as alkynes, alkenes, β-hydroxy ketones, aldehydes, allylic alcohols, and allenes (see scheme, E = electrophile).

Tandem Pd/C-catalyzed reductive coupling and dehalogenation of benzylic halides

High-yield reductive homocoupling of benzotrichloride and benzal chloride followed by consecutive reductive dechlorination to 1,2-dichlorostilbene and stilbene is effected in the presence of sodium formate as the reducing agent and Pd/C catalysts. Copyright Taylor & Francis, Inc.

Inter- and innermolecular reactions of chloro(phenyl)carbene

Supramolecular photolyses of 3-chloro-3-phenyl-3H-diazirine (8) were performed within cyclodextrin (CyD) hosts to determine whether these toroidal inclusion compounds could alter the reactivity of the ensuing carbene reaction intermediate, chloro(phenyl)carbene (9). Remarkably, no intramolecular products stemming from carbene 9 could be detected. Instead, modified CyDs were formed via so-called innermolecular reactions. Hence, diazirine 8 was photolyzed in various conventional solvents to gauge the intermolecular reactivity of carbene 9. Relevant results were used to rationalize the CyD innermolecular reaction products.

Reaction of Aromatic and Unsaturated Compounds with the Potassium Permanganate/HCI (HBr) Acetonitrile Reagent

Addition of hydrochloric or hydrobromic acid to a solution of potassium permanganate in acetonitrile produced a homogeneous mixture, which is suitable for laboratory chlorination or bromination, respectively. Aromatic compounds more reactive than alkylbenzenes can be chlorinated or brominated without additional catalyst. Alkenes and alkynes give the corresponding vicinal dihaloalkanes and vinyl halides. All reactions complete within two hours under mild condition (25-60 °C) with excellent to moderate yields.

A laser flash photolysis study of carbonyl ylides of arylchlorocarbenes: Kinetics and reversibility of the formation, cyclization, and cycloaddition

Carbonyl ylides formed from (p-nitrophenyl)chlorocarbene or phenylchlorocarbene and acetone or benzaldehyde have been studied by laser flash photolysis. The rate constants for the formation of these ylides, for their cyclization to oxiranes, and for some addition reactions have been measured. Electron-withdrawing substituents on the carbene increase the rate of ylide formation and decrease the rate of cyclization. The trapping of carbonyl ylide and para-substituted benzaldehydes gave a Hammett's ρ value equal to +1.0. The dual role of benzaldehyde, first as a constituent of the ylide and second as a trapping agent, has been demonstrated. Kinetic analysis indicates that an equilibrium exists between the phenylchlorocarbene, the acetone, and the corresponding ylide, with an equilibrium constant around 0.27 M-1 at 300 K.

Reductive Coupling by Chromium(0) - (Bibenzyl)- and (Stilbene)tricarbonylchromium(0) Complexes by a One-Pot Reaction from Benzylic Halides

Reaction of Cr(CO)3(NH3)3 with benzylic mono-, di-, and trihalides leads to the formation of 1,2-diarylethanes, -ethenes, and diphenylethyne in satisfactory yields.Di(halomethyl)benzene derivatives yield product mixtures containing both reduction products and coupling products.With a higher excess in chromium(0), under otherwise unchanged reaction conditions, the corresponding (arene)tricarbonylchromium(0) complexes of the coupling products are formed in a one-pot reaction from the benzylic halides.

A PHENYLCARBENE TRANSFER SYSTEM

Treatment of (α,α-dichlorobenzyl)trimethylsilane with potassium fluoride/18-crown-6 ether/diglyme transfers phenylchlorocarbene to a number of carbenophiles at room temperature.