Isomer distribution of tertiary alcohols

The stereospecificity of the hydrocarbon ozonation was investigated by measuring the isomer distribution of tertiary alcohols formed on ozonating cis- and fmri5-l,2-dimethylcyclohexane and cis- and trans-DecR-lin. Other oxidation products are formed in these ozonations, but the tertiary alcohols are easily separated from these by gas chromatography. Some results are shown in Table II. The observed isomer distributions of tertiary alcohols are independent of time for up to 3 hours ozonation... 

Table II. Isomer Distribution of Tertiary Alcohols from the Ozonation of cis- and mws-Hydrocarbons...

The effect of various additives on the isomer distribution of tertiary alcohols, obtained from ct5-l,2-dimethylcyclohexane, was investigated to determine the reason for the lack of complete stereospecificity in the ozonation. The results are summarized in Table III. None of the addi-... 

The ability of the Fe (DPAH)2/02/PhNHNHPh system (where PhNHNHPh is a mimic for flavin rednctases) to monooxygenate saturated hydrocarbons closely parallels the chemistry of the methane monooxygenase proteins. However, the enzyme oxygenates 2-Me-bntane with an isomer distribution of 82% primary alcohol, 10% secondary, and 8% tertiary. The present model gives a distribution of 21% primary, 29% secondary, and 50% tertiary. Clearly the protein affords a cavity that is selective for -CH3 groups. 

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