169172-22-9

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 1826-67-1 vinyl magnesium bromide 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 149946-79-2 1-(4'-(trifluoromethyl)phenyl)-allylalcohol 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 125617-18-7 3-(4-trifluoromethylphenyl)-2-propen-1-ol 
• 101466-85-7 ethyl (E)-4-trifluoromethylcinnamate 
• 2062-26-2 3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid 

Downstream Products

• 562811-22-7 (2E)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-yl acetate 
• 1337953-53-3 (E)-4-methyl-2-phenyl-2-(3-(4-(trifluoromethyl)phenyl)allyl)oxazol-5(2H)-one 

Relevant academic research and scientific papers

Size-Exclusion Borane-Catalyzed Domino 1,3-Allylic/Reductive Ireland–Claisen Rearrangements: Impact of the Electronic and Structural Parameters on the 1,3-Allylic Shift Aptitude

The reductive Ireland–Claisen rearrangement through borane-mediated hydrosilylation is reported. The method employs a borane catalyst with a special structural design and affords access to synthetically relevant products with high diastereoselectivity. Depending on electronic and structural parameters, the reaction can be coupled with a 1,3-allylic shift, thus the valence isomer of the Ireland–Claisen product is formed.

Hydroxymethylation beyond Carbonylation: Enantioselective Iridium-Catalyzed Reductive Coupling of Formaldehyde with Allylic Acetates via Enantiotopic π-Facial Discrimination

Chiral iridium complexes modified by SEGPHOS catalyze the 2-propanol-mediated reductive coupling of branched allylic acetates 1a-1o with formaldehyde to form primary homoallylic alcohols 2a-2o with excellent control of regio- and enantioselectivity. These

[(NHC)Au1]-catalyzed rearrangement of allylic acetates

Equation Presented [(NHC)AuCl] complexes (NHC = N-heterocyclic carbene), in conjunction with a silver salt, were found to efficiently catalyze the rearrangement of allylic acetates under both conventional and microwave-assisted heating. The optimization of several reaction parameters (solvent, silver salt, and ligand) as well as a study of the reaction scope are reported. The steric hindrance of the ligand bound to gold was found crucial for the outcome of the reaction as only extremely bulky ligands permitted the isomerization.

The photochemistry of ring-substituted cinnamyl acetates

The photochemistry of the (E)-cinnamyl acetates ((E)-1-aryl-3-propenyl acetates, 8a-8e) with substituents H, 4-CH3O, 3-CH3O, 4-CF3, and 3-CF3, respectively, was examined in both cyclohexane and methanol solvents. Alkene isomerization (E to Z) occurred more efficiently than other reactions and evidence is presented that this process occurs from the excited triplet state. In a slower process, 1,3-migration of the acetoxy group led to the rearranged 3-aryl-3-propenyl acetate isomers (9a-9e) as the major pathway, particularly in cylohexane. In methanol, the isomeric ethers 3-aryl-3-methoxypropene (14) and 1-aryl-3-methoxypropene (15) were formed by reaction of methanol with the photochemically generated cation. The combined yield of 14 and 15 (95% and 5%, respectively) was quantitative for the 4-methoxyphenyl compound (8b). Independent irradiations of the isomers 9a-9c demonstrated that the ethers 14 and 15 were primary photoproducts from 8 and not secondary photoproducts from 9. Fluorescence quantum yields and excited singlet state lifetimes indicated that the reactions, other than the E to Z isomerization, are from the excited singlet state.