DEPLACEMENTS HOMOLYTIQUES INTRAMOLECULAIRES-I; ETUDE DE LA DECOMPOSITION DU PERPENTENE-4 OATE DE t-BUTYLE DANS LES CYCLANES. SYNTHESE DE CYCLOALKYL-5 PENTANOLIDES-4

Article abstract of DOI:10.1016/S0040-4020(01)91505-4

The thermolysis of t-butyl-4-peroxypentenoate 1, in cyclohexane led to several compounds; the main product was 5-cyclohexyl-4-pentanolide (yield 35percent).Hypotheses are proposed to explain their formation.The lactone could be obtained by two different mechanisms: a concerted one and a two-step one (cyclohexyl radical addition to the double bond of the perester leading to a discrete radical followed by an intramolecular displacement of a t-butoxyl radical).The thermolysis of 1 has synthetic interest: several original 5-cycloalkyl-4-pentanolides have been obtained by this way.