9-Decalyl hydroperoxide

Two-carbon ring expansion. Some year. ago Criegee- reported that the benzoate (1) of 9-decalyl hydroperoxide rearranges on standing by way of l-benzoyloxy-1,6-epox-ycyclodecane (2) to the hydroxycyclodecanone L... 

Decomposition of the /rtin -decalyl perester A gives a 9 1 ratio of trans cis hydroperoxide product at all oxygen pressures studied. The product ratio from the cis isomer is dependent on the oxygen pressure. At 1 atm O2, it is 9 1 trans cis, as with the trans substrate, but this ratio decreases and eventually inverts with increasing O2 pressure. It is 7 3 cis trans at 545 atm oxygen pressure. What deduction about the stereochemistry of the decalyl free radical can be made from these data ... 

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