35818-84-9Relevant academic research and scientific papers
Organic Peroxides, XXIV. - On the Barton Type Cyclization of Organic Hydroperoxides
Kropf, Heinz,Wallis, Helmut von
, p. 610 - 623 (2007/10/02)
On the earlier reported cyclization conditions the hydroperoxides 1e-g yield the 1,2-dioxolanes 2e-g, but the hydroperoxide 1d gives the 1,2-dioxocane 2d only in low yield.On the reaction of the hydroperoxides 1a and 1b as examples for the reported cyclization reactions the compounds obtained besides the cyclization products are ascertained particularly (symmetric and unsymmetric dialkyl peroxides 4 and 7, alcohols 3, carbonyl compounds 5 and 6).The hydroperoxides 1h and 1i yield the symmetric and unsymmetric dialkyl peroxides as peroxidic compounds only.The hydrocarbons 10a and 10b as well as the alcohols 3a and 3b do not react on the cyclization conditions. - Reaction of 1a with lead(IV) acetate in acetic acid yields the alkyl methyl peroxide 9a, in propionic acid/n-pentane the alkyl ethyl peroxide 9b. - Cer(IV) sulfate reacts as cyclodehydrogenation reagent also. - The earlier postulated Barton type mechanism was made certain on the reasons of the results.
