66820-08-4

Upstream product

• 86509-74-2 c-4-t-butyl-c-2,c-6-dimethylcyclohexan-r-1-ol 
• 49714-32-1 c-4-t-butyl-r-2,t-6-dimethylcyclohexanone 
• 86509-74-2 t-4-t-butyl-c-2,t-6-dimethylcyclohexan-r-1-ol 
• 879-97-0 2,6-dimethyl-4-tert-butylphenol 
• 75-91-2 tert.-butylhydroperoxide 

Downstream Products

• 66820-12-0 (1S,3S,5R)-1-tert-Butyl-3,5-dimethyl-cyclohexane 
• 66820-11-9 c-5-t-butyl-1,r-3-dimethylcyclohexene 
• 66820-11-9 t-5-t-butyl-1,r-3-dimethylcyclohexene 

Relevant academic research and scientific papers

Stereoelectronic Effects in Hydrogen-atom Transfer Reactions of Substituted Cyclohexyl Radicals

Thermolysis of the peroxyoxalates (1)-(7) and the diacyl peroxides (8)-(11) in cyclohexane at 100 deg C gives cycloalkenes and cycloalkanes by hydrogen-atom transfer reactions of the initially formed conformationally biased 4-t-butyl-, 4-t-butyl-cis,cis-2,6-dimethyl-, 4-t-butyl-cis,trans-2,6-dimethyl-, 4-t-butyl-cis-2-methyl-, 4-t-butyl-trans-2-methyl-, and 5-t-butyl-cis-2-methylcyclohexyl radicals (12)-(17).The composition of the product mixtures indicates that transfer of axial β-hydrogen atoms occurs more rapidly than does transfer of equatorial β-hydrogen atoms.These results support the hypothesis that homolytic fission of a C-H bond is favoured when it lies chlose to the plane of an adjacent semi-occupied orbital.