85982-06-5Relevant academic research and scientific papers
Organic Peroxides, XXV. - The Reactivity of Benzylic Methyl Groups at the Barton Type Cyclization of Organic Hydroperoxides
Kropf, Heinz,Wallis, Helmut von,Bartnick, Lily
, p. 624 - 634 (2007/10/02)
On the earlier reported cyclization conditions the hydroperoxides 1a-d yield the 2,3-dioxabenzacyclooctenes 3a, 3b and 2,3-dioxabenzocyclononenes 3c, 3d as well as the 1,2-dioxolanes 4a, 4b and 1,2-dioxanes 4c, 4d, respectively.Starting from the hydroperoxide 2 the 1,2-dioxolane 7 is the only cyclic peroxide obtained.The symmetric and the unsymmetric dialkyl peroxides 5, 6, 8, and 9 are obtained in all cases. - On the reaction of the hydroperoxides 1a, 1c, and 1d in acetic acid the cyclization is reduced to a very small extend.The symmetric dialkyl peroxides 5a, 5c, and 5d and the alkyl methyl peroxides 10a, 10c, and 10d are obtained in low yields. - The relatively high yields of the peroxides 3 are discussed on the basis of stereo-electronic effects.
