INTRAMOLECULAR HOMOLYTIC DISPLACEMENTS 7 - FREE RADICAL ADDITIONS TO UNSATURATED PEROXY COMPOUNDS : SYNTHESIS OF OXYGENATED HETEROCYCLES

Article abstract of DOI:10.1016/S0040-4020(01)97183-2

Free radical additions of hydrogen donor solvents to tert-butyl perpent-4-enoate have given 4-substituted γ-butyrolactones, with yields of 50 percent 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 5-methyl-perhex-4-enoate and tert-butyl-3-methyl-but-2-enyl peroxide.