107909-13-7

Upstream product

• 58824-48-9 1-(4-methylphenyl)-2-propen-1-ol 
• 108-24-7 acetic anhydride 
• 104-87-0 4-methyl-benzaldehyde 
• 3536-96-7 vinylmagnesium chloride 
• 75-36-5 acetyl chloride 
• 106-38-7 para-bromotoluene 
• 3333-13-9 p-allyltoluene 
• 60604-09-3 3-phenylpropane-3,3-d₂ 
• 64-19-7 acetic acid 

Downstream Products

• 111133-19-8 trimethyl<3-(4-methylphenyl)-2-propenyl>silane 
• 164527-43-9 phosphoric acid diethyl ester 3-p-tolylallyl ester 
• 77134-00-0 (E)-4-methylcinnamyl acetate 
• 88044-28-4 Benzyl-((E)-3-p-tolyl-allyl)-amine 
• 360066-00-8 benzyl-(1-p-tolyl-allyl)-amine 
• 164527-49-5 dimethyl (E)-2-(3-(4-methylphenyl)allyl)malonate 
• 1152652-44-2 (E)-benzyl-(4-fluorobenzyl)-(3-p-tolylallyl)amine 
• 1152652-69-1 (E)-methyl-phenyl-(3-p-tolylallyl)amine 
• 1398400-18-4 (R)-3-(1-tolylallyl)furan-2(5H)-one 
• 1398398-16-7 (R)-3-(1-phenylallyl)furan-2(5H)-one 
• 1380438-84-5 (-)-(R)-(E)-3-(1,3-diphenylallyl)furan-2(5H)-one 
• 1398400-01-5 (R,E)-3-(3-(6-methylpyridin-3-yl)-1-phenylallyl)furan-2(5H)-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.

Kinetic Resolution of Racemic and Branched Monosubstituted Allylic Acetates by a Ruthenium-Catalyzed Regioselective Allylic Etherification

We demonstrated the kinetic resolution of racemic and branched monosubstituted allylic acetates by a ruthenium-catalyzed regioselective allylic etherification. The reaction was effectively catalyzed by the chiral ruthenium catalyst, which was generated by [RuCl2(p-cymene)]2 and (S,S)-iPr-pybox and a catalytic amount of TFA, and both the allylic etherification product and recovered allylic acetate were obtained as an enantiomerically enriched form with up to a 103 s value.

Mechanistic investigation of palladium-catalyzed allylic C-H activation

The mechanism for the palladium-catalyzed allylic C-H activation was investigated using a combination of experimental and theoretical methods. A Hammett study revealed a buildup of a partial negative charge in the rate-determining step, and determination of the kinetic isotope effect (KIE) indicated that the C-H bond is broken in the turnover-limiting transition state. These experimental findings were further substantiated by carrying out a detailed density functional theory (DFT)-based investigation of the entire catalytic cycle. The DFT modeling supports a mechanism in which a coordinated acetate acts as a base in an intramolecular fashion during the C-H activation step. The reoxidation of palladium was found to reach an energy level similar to that of the C-H activation. Calculations of turnover frequencies for the entire catalytic cycle for the C-H alkylation were used to acquire a better understanding of the experimental KIE value. The good correspondence between the experimental KIE and the computed KIE values allows discrimination between scenarios where the acetate is acting in an intramolecular fashion (C-H alkylation) and an intermolecular fashion (C-H acetoxylation and C-H amination).

Mechanism of cycloisomerisation of 1,6-heptadienes catalysed by [(tBuCN)2PdCl2]: Remarkable influence of exogenous and endogenous 1,6- And 1,5-diene ligands

The mechanism of the highly regioselective cycloisomerisation of dimethyl hept-1,6-dienyl-4,4-dicarboxylate (1) by a neutral pre-catalyst, [(tBuCN) 2PdCl2] (8), to generate dimethyl 3,4-dimethylcyclopent-2- ene-1,1-dicarboxylate (3)

Regiocontrol and Stereoselectivity in Tungsten-Bipyridine Catalysed Allylic Alkylation

Tungsten-bipyridine complexes, generated in situ, catalyse the allylic alkylation of isocinnamyl methyl carbonate by dimethyl sodiomalonate with complete syn-stereoselectivity.When para substituted aryl-allyl methyl carbonates are employed, the regioselectivity correlates with Swain-Lupton parameters.Cross-over experiments demonstrate that the reactions do not proceed via the conventional 0> -> II allyl>+ -> 0 allyl-Nu> catalytic cycle.

Chirale Phosphanodihydrooxazole in der asymmetrischen Katalyse: Wolfram-katalysierte allylische Substitution

Stichworte: Alkylierungen * Asymmetrische Synthesen * Dihydrooxazole * Katalyse * Wolframverbindungen

THE NITROGENATED ALLYLIC SYSTEM AS AN INTRAMOLECULAR NUCLEOPHILE: A NEW ROUTE TO PYRAZOLES

A new route to pyrazoles via the cyclization of N-allyl-N-nitrosoamides is described.