102434-81-1

Upstream product

• 763-29-1 2-Methyl-1-pentene 
• 13389-70-3 bis(4-methylphenyl)methyl chloride 

Relevant academic research and scientific papers

Thermochemical Study of the Addition of Carbenium Ions to Alkenes

Scales of carbenium ion stabilities have been obtained from 1H NMR equilibrium studies of mixtures of partly ionized para-substituted diarylmethyl chlorides in CD2Cl2/BCl3 at -70 deg C and via calorimetric determination of the heats of ionization (ΔHi) of the alkyl chlorides (Ar2CHCl + BCl3 -> Ar2CH+BCl4-) in CH2Cl2/BCl3 at -70 deg C.The heats of the reactions of diarylmethyl tetrachloroborates with 2-methyl-1-pentene (Ar2CH+BCl4- + CH2=C(CH3)C3H7 -> Ar2CHCH2C(CH3)ClC3H7 + BCl3), which were determined by low-temperature calorimetry, increase from -53.1 kJ/mol for (H3CC6H4)2CH+BCl4- to -33.0 kJ/mol for the better stabilized (H3COC6H4)(H3CC6H4)CH+BCl4-.In contrast, the heats (ΔHa) of the Lewis acid catalyzed additions of the corresponding para-substituted diarylmethyl chlorides to 2-methyl-1-pentene are independent of the para substituents (ΔHa=-86.5 +/-2.7 kJ/mol).Similar values of ΔHa were obtained for the addition of p-anisylphenylmethyl chloride to trimethylethylene, styrene, β-methylstyrene, and isoprene. ΔHa is predominantly determined by the conversion of a ?(C=C) into a ?(C-C) bond, and the heats of addition of diarylmethyl tetrachloroborates to alkenes in CH2Cl2 are given by the equation ΔHb=(9.5 +/- 6.3 pKR+) kJ/mol.

Addition reactions of diarylcarbenium ions to 2-methyl-1-pentene: Kinetic method and reaction mechanism

A kinetic method that allows the determination of reactivities of carbenium ions toward alkenes is described: Diarylmethyl chlorides (1) are completely ionized by BCl3 in CH2Cl2 to give colored solutions of diarylcarbenium

Relative Reactivities of Alkyl-Substituted Alkenes and Cycloalkenes towards Diarylcarbenium Ions

The relative reactivities of alkyl-substituted alkenes 4 towards diarylmethyl cations 2 generated in situ from diarylmethyl chlorides 1 and Lewis acids were determined by competition experiments.The relative reactivities were almost independent of the nature of the Lewis acid. Eventual differences of the solvation free enthalpies of various activated complexes are, therefore, independent of the nature of the gegen ions.The rate acceleration by methyl groups - 6-50 by CH3 at the attacked vinylic position and approximately 104 at the developing carbenium centre - indicates a scarcely bridged transition state.

Relative Reactivity of Conjugated Alkenes towards Diarylcarbenium Ions

The relative reactivities of conjugated alkenes 3 towards diarylcarbenium ions 2 have been determined by competition experiments.For 2-substituted propenes H2C=C(CH3)R we found the following reactivity sequence with respect to R: cyclopropyl >> alkyl >/=