17936-67-3

Upstream product

• 1866-39-3 trans-p-methylcinnamic acid 
• 4974-59-8 2,2-dichloro-4'-methylacetophenone 
• 122-00-9 para-methylacetophenone 
• 75-09-2 dichloromethane 
• 104-87-0 4-methyl-benzaldehyde 
• 17936-73-1 2,2,2-trichloro-1-p-tolyl-ethanol 

Downstream Products

• 73040-55-8 N-(5-p-tolyl-thiazol-2-yl)-acetamide 
• 61693-88-7 C₁₅H₁₃Cl₃ 
• 34025-31-5 α-Hydroxy-p-tolylacetaldehyd 
• 73805-19-3 trans-β-chloro-p-methylstyrene oxide 
• 73040-54-7 5-(p-tolyl)thiazol-2-amine 
• 26204-07-9 1,1-dichloro-2,2-bis(p-methylphenyl)ethane 

Relevant academic research and scientific papers

Reaction of α,β-Unsaturated Carboxylic Acids with Manganese(III) Acetate in the Presence of Chloride Ion

The reaction of 3-phenylpropenoic acids with manganese(III) acetate - Cl- complex yielded 1,2,2-trichloro-1-phenylethanes, 1-acetoxy-2,2-dichloro-1-phenylethanes, and 2,2-dichloro-1-phenylethanols. (E)-2,3-Diphenylpropenoic acids gave 2,2-dichloro-1,2-diphenylethanones and 2-acetoxy-1,2-diphenylethanones. 3,3-Diphenylpropenoic acids yielded 2,2-dichloro-1,1-diphenylethenes, 1-acetoxy-2,2-dichloro-1,1-diphenylethanes, 2,2-dichloro-1,1-diphenyl-1-ethanols, and 2-hydroxy-2,2-diphenylethanal.Fluorenylideneacetic acid gave 9-chloro-9-(dichloromethyl)fluorene, 9-acetoxy-9-(dichloromethyl)fluorene, and 9-fluorenone. 1-Cyclohexenecarboxylic acid yielded 1,2-dichlorocyclohexanecarboxylic acid and 1-acetoxy-2-chlorocyclohexanecarboxylic acid.The reaction can be explained in terms of a free-radical mechanism involving manganese(III) acetate - Cl- complexation, addition of Cl. radical, decarboxylation, and the oxidation of chloroethenes which are the reaction intermediates.

Molecular Rearrangements. 13. Kinetics and Mechanism of Rearrangements of Some Ring-Substituted α-Chlorostyrene Oxides and trans-β-Chlorostyrene Oxides.

The synthesis of certain phenyl-substituted derivatives of the isomeric trans-β-chlorostyrene oxides (6) and α-chlorostyrene oxides (7) are reported.The kinetics of rearrangement of 6 (X = p-CH3, H, p-Br, m-Cl, p-NO2) to phenylchloroacetaldehydes (12) in CCl4 buffered by Na2HPO4 and 7 (X = p-CH3, H, p-NO2) to ω-chloroacetophenones in CCl4 were determined by following the rates of disappearance of the α-chloro epoxide and formation of the α-chloro carbonyl product.These substituent effects at 130 deg C were correlated with ?+ constants, yielding ρ values of-3.5 and -0.57 for the rearrangements of 6 and 7, respectively.In nitrobenzene solvent, the kC6H5NO2/kCCl4 for 6 was 180 and for 7 was 1740, the latter solvent effect attributed to nucleophilic solvent participation.It was concluded that these thermal rearrangements of 6 and 7 occur by disrotatory Cβ-O bond heterolysis to yield the corresponding α-keto carbonium-chloride ion pairs.