85688-99-9

Upstream product

• 27129-86-8 1-bromomethyl-3,5-dimethylbenzene 
• 594-19-4 tert.-butyl lithium 
• 2745-54-2 3,5-dimethylbenzyl chloride 
• 100093-97-8 4-(2,2-Dimethylpropyl)-2-methyl-1-(2-methyl-1,3-dioxolan-2-yl)-4-penten-2-ol 
• 927-83-3 di-t-butyldiazene 
• 108-88-3 toluene 
• 108-67-8 1,3,5-trimethyl-benzene 
• 123-54-6 acetylacetone 
• 75-65-0 tert-butyl alcohol 
• 21954-82-5 (tert-Butyl)(methyl)malononitril 
• 507-20-0 tertiary butyl chloride 

Relevant academic research and scientific papers

1-(2,2-Dimethylpropyl)-3,5-dimethylbenzene, an Unexpected Side Product

The title compound 4 is formed in fair yield in addition to the oligomers of isobutene during synthesis of 3-tert-butyl-2,4-pentanedione (2) from 2,4-pentanedione (1) with tert-butylalcohol and perchloric acid in nitromethane.Acid-catalyzed condensation of 1 with isooctene 5 is discovered to be responsible for the formation of 4.This reaction yields other meta-neopentyl-substituted benzene derivatives (19,20,21) with several β-diketones.

Substituent Effects on the C-C-Bond Strength, 3. The Thermal Stability of 2,2-Disubstituted Malononitriles

The products, the rate constants and the activation parameters of the homolytic thermal decomposition of a series of malononitriles 8a - e were determined.A linear correlation is found between ΔG* (300 deg C) and the strain enthalpies Hsp of 8 as deduced from force field calculations (MM2 force field).From this correlation and a comparison with the corresponding relationship for Cq-Cq alkanes 9.2 kcal*mol-1 resonance energy of 1,1-dicyanoalkyl radicals 10 is estimated.The relationships between strain enthalpy Hsp, structure and barriers to internal rotation for the compounds 8 are discussed briefly.

Chemistry of the tert-Butyl Radical: Polar Character, ρ Value for Reaction with Toluenes, and the Effect of Radical Polarity on the Ration of Benzylic Hydrogen Abstraction to Addition to Aromatic Rings

We have reexamined the reactions of tert-butyl radicals with toluenes and have obtained a ρ value of 0.49 +/- 0.04 at 80 deg C.The new, independent system involves the quantification of all of the principal products from the reaction of tert-butyl radicals with mixtures of toluene and substituted toluene.Five major products contain benzyl fragments and are formed in significant yields: two symmetrical bibenzyls, the cross bibenzyl, and the two neopentylbenzenes that result from combination of tert-butyl and the two benzyl radicals.Attack on the side chain is a major reaction of free tert-butyl radicals and is the only significant reaction that they undergo other than cage and termination reactions. tert-Butyl radicals do not add to the ring of toluenes.Data on the relative rates of addition to benzenes and hydrogen abstraction from toluenes are collected for a series of radicals including hydrogen atoms; methyl, isopropyl, and tert-butyl radicals; and p-nitrophenyl, p-bromophenyl, and phenyl radicals.The data demonstrate that more electrophilic radicals have a larger tendency to add to rings whereas more nucleophilic radicals have a larger tendency to abstract benzylic hydrogens.