4845-03-8Relevant academic research and scientific papers
Initiated tert-Butyl Hydroperoxide-loaded Low-temperature Autoxidation of Alkenes: Alternative Hydroperoxide Syntheses and the Preparation of a Complete Set of Reference Material
Courtneidge, John L.,Bush, Melanie,Loh, Lay-See
, p. 1539 - 1548 (2007/10/02)
A complete set of characterization data for the allylic hydroperoxides prepared from 1-methylcyclohexene and the isomeric 4-methyloct-4-enes is presented.The data relies upon the preparation of allylic hydroperoxides by tert-butyl hydroperoxide-loaded autoxidations, singlet-ene oxidations and nucleophilic substitution reactions.Appropriate allylic alcohols and relevant scission products have been prepared to support the assignments given.
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
Courtneidge, John L.,Bush, Melanie
, p. 1531 - 1538 (2007/10/02)
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.
Studies on the Autoxidation of Some Monocyclic Olefins
Blau, K.,Mueller, U.,Pritzkow, W.,Schmidt-Renner, W.,Sedshaw, Z.
, p. 915 - 932 (2007/10/02)
The autoxidations of cyclopentene, cyclohexene, cycloheptene, cyclooctene, cycloocta-1,5-diene, 1-methylcyclopentene, 1-methylcyclohexene, 1-methylcycloheptene, 1-methylcyclooctene, methylene cyclopentene, and methylene cyclohexene with pure oxygen under normal pressure were studied.The epoxides formed were determined gaschromatographically.In most cases also the products of allylic oxidation were analyzed and their structures elucidated after reduction to the corresponding allyl alcohols.The portions of high boiling or polymeric products which could not be detected gaschromatographically and also the real yields of epoxides were determined by balance experiments in the presence of inert internal standards.
