Intramolecular homolytic displacements 7—Free radical additions to unsaturated peroxy compounds: Synthesis of oxygenated heterocycles

B Maillard, A Kharrat, F Rakotomanana, E Montaudon…

Index: Maillard, Bernard; Kharrat, Abdelmajid; Rakotomanana, Felicien; Montaudon, Evelyne; Gardrat, Christian Tetrahedron, 1985 , vol. 41, # 19 p. 4047 - 4056

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Citation Number: 15

Abstract

Free radical additions of hydrogen donor solvents to tert-butyl perpent-4-enoate have given 4-substituted γ-butyrolactones, with yields of 50% or greater. Such reactions applied to allyl- tert-butyl peroxide have produced 2, 3-epoxypropanation of these solvents. Similar addition- elimination processes occurred with tert-butyl 4-methyl-perpent-4-enoate, tert-butyl 2, 2- dimethyl-perpent-4-enoate and tert-butyl-methallyl peroxide, but they failed with tert-butyl ...