77028-63-8

Upstream product

• 66639-74-5 2-Methyl-1-phenylallyllithium 
• 5912-93-6 1-bromo-2-methyl-1-phenyl-1-propene 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 83126-01-6 (E)-1-(3-bromo-2-methylprop-1-en-1-yl)benzene 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 121525-02-8 2-Chloro-2-(⁽²⁾H₃)-methyl-1-phenyl-(3,3,3-⁽²⁾H₃)-propane 
• 66639-74-5 2-Methyl-1-phenylallyllithium 
• 67-56-1 methanol 

Downstream Products

• 77028-69-4 C₁₅H₁₇⁽²⁾HO₅ 
• 77028-65-0 2-Hydroxy-2-((Z)-2-methyl-3-phenyl-allyl)-malonic acid dimethyl ester 
• 77028-67-2 2-Hydroxy-2-((E)-2-methyl-3-phenyl-allyl)-malonic acid dimethyl ester 
• 77028-84-3 C₁₅H₁₇⁽²⁾HO₅ 
• 77028-85-4 C₁₅H₁₇⁽²⁾HO₅ 

Relevant academic research and scientific papers

Contra-Thermodynamic Positional Isomerization of Olefins

A light-driven method for the contra-thermodynamic positional isomerization of olefins is described. In this work, stepwise PCET activation of a more substituted and more thermodynamically stable olefin substrate is mediated by an excited-state oxidant an

Differential NMR Shielding by Phenyl, Assigned from Chemical Labelling and (Z,E) Equilibration

Unequivocal NMR assignments of the (E,Z) isomeric pairs 3 and 8 are possible by (Z,E) equilibration.Deprotonation of 2-methyl-1-phenylpropene (1) with n-BuLi under any conditions gives only a single allyl-metal derivative 2.Methylation of the latter gives

Borderline between E1 and E2 Mechanisms. Bimolecular Base-Promoted Elimination via Ion Pairs Competing with Concerted E2 Elimination

The solvolysis of 2-chloro-2-methyl-1-phenylpropane (1) in methanol or in 25 vol percent acetonitrile in water at 25 deg C yields substitution product 2 (ether or alcohol) and the two elimination products 3 and 4.The olefin fraction in the aqueous solution does not increase significantly in the presence of 0.75 M sodium hydroxide.In methanol, on the other hand, the fraction of 3 and 4, the ratio /, and the rate of disappearance of 1 increase with methoxide ion concentration.The kinetic isotope effects (k12H + k13H + k14H)/(k12d2 + k13d2 +k14d2) = 1.41 and 1.42, measured for the solvolysis of the dideuterated analogue d2-1 in water/acetonitrile and in methanol, respectively, are too large to be secondary effects on a rate-limiting ionization step, but they suggest reaction via a reversibly formed carbocationic intermediate.The solvolysis of the hexadeuterated analogue d6-1 exhibits "normal" secondary kinetic isotope effects, (k12H + k13H + k14H)/(k12d6 + k13d6 + k14d6) = 1.79 and 1.81 in water/acetonitrile and methanol, respectively.The presence of 2 M NaOMe increases the isotope effect for d2-1 to 2.4 but decreases the effect for d6-1 to 1.35.These results indicate that 3 is formed by a parallel methoxide-promoted one-step concerted rout (E2) and that such a route is not significant for the formation of 4.The isotope effect for the E2 reaction is estimated as kH/kd2 = 4.9 (on the basis of the assumption that the elimination product ratio / for the carbocationic route is not affected by MeO(1-)).

2-Methyl-1-phenyl-1-propenyllithium. A Vinyllithium Derivative Showing Catalyzed Transmetalation

Full preparative and kinetic details are given for the apparent vinyl-to-allyl anion rearrangement of the title compound 1.The rapid and quantitative formation of the allyllithium derivative 7 is shown to be catalyzed by 2-methyl-1-phenyl-1-propene (2).An intermolecular transmetalation mechanism with de-aggregation and ionization steps is suggested to explain the orders of reaction, parameters of activation, and solvent dependency.