124783-72-8Relevant academic research and scientific papers
1-(Cyclohex-1-enyl)cyclohexyl Hydroperoxide: Intramolecular Propagation of Autoxidation as an Alternative Reaction to Allylic Rearrangement
Davies, Alwyn G.,Davison, Ian G. E.,Schiesser Carl H.
, p. 742 - 744 (1989)
The allylperoxyl radical derived from 1-cyclohex-1-enyl)cyclohexyl hydroperoxide does not undergo allylic rearrangement, but in the presence of oxygen it undergoes autoxidation with an intramolecular propagation step, leading to the formation of 1-(6-hydr
Reactivities of Some Allylic Hydroperoxides toward Allylic Rearrangement and Related Reactions
Dang, Hai-Shan,Davies, Alwyn G.,Davison, Ian G. E.,Schiesser, Carl H.
, p. 1432 - 1438 (2007/10/02)
The allylic rearrangement has been studied of the hydroperoxides that are formed when singlet oxygen reacts with epicholesterol, Δ9,10-octahydronaphthalene, 2,3-dimethylbut-2-ene, cyclopentylidenecyclopentane, and cyclohexylidenecyclohexane.The reactivity in this sense decreases in the above sequence. 1-(Cyclopent-1-enyl)cyclopentyl hydroperoxide rearranges only slowly, but in the presence of triplet oxygen it reacts to give 1-(5-hydroperoxycyclopent-1-enyl)cyclopentyl hydroperoxide, and 1-(cyclohex-1-enyl)cyclohexyl hydroperoxide does not rearrange and shows only the reaction with oxygen to give 1-(6-hydroperoxycyclohex-1-enyl)cyclohexyl hydroperoxide.The various factors that affect the rates of these reactions are discussed.It is suggested that the reactivity and regioselectivity in the autoxidation which leads to the formation of dihydroperoxides implies that the reaction involves not the usual two-step propagation sequence, but a three-step sequence in which the chain carriers are a cycloalkenyl radical, a cycloalkenylperoxyl radical, and a cycloalkylperoxyl radical.
