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Initiated, tert-Butyl Hydroperoxide-loaded, Low-temperature Autoxidation of Alkenes: A Chemoselective Synthesis of Allylic Hydroperoxides, allowing Analysis of the Regioselectivity of Hydrogen Atom Abstraction from some Unsymmetrically Substituted Substrates

DOI: 10.1039/P19920001531

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1531 - 1538 (1992)

Update date:2022-08-11

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Authors:

Courtneidge, John L.Courtneidge, John L.

Bush, MelanieBush, Melanie

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Article abstract of DOI:10.1039/P19920001531

A method for the preparation of allylic hydroperoxides is introduced: the method involves the rapid, low-temperature, initiated autoxidation of an alkene (in these instances 1-methylcyclohexene and the isomeric 4-methyloct-4-enes) in the presence of tert-butyl hydroperoxide.The success of the method relies upon the selectivity of hydrogen atom abstraction from the substrate by the chain-carrying tert-butylperoxyl radicals, according to the preference for formation of the most stable intermediate allylic radicals, and the reduced rates of chain termination via thesesame radicals.The method gives a regioselectivity for attack broadly in agreement with predictions from Bolland's rules, and a sufficiently high chemoselectivity for allylic hydroperoxide formation that ready isolation of these products in good yields is achieved.

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Product name:Hydroperoxide, 1-methyl-2-cyclohexen-1-yl

Cas No:18428-16-5

18428-16-5

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