REACTIVITY OF 1-CYCLOPROPENE-1-LACTONES DEPENDENT ON THE SUSBSTITUTION DEGREE

Article abstract of DOI:10.1016/S0040-4020(01)88440-4

Reaction of the α-chloro lactone 10 with KOtBu gives the butoxy lactones 21 and 22; the seven membered derivative 11 leads 23 as the only isolable product.Formation of the α-substitution product 21 as well as the enhanced instability of the intermediates 12 and 13 in comparison to their methyl substituted homologues 5 and 6 show the kinetical stabilization by a methyl group at C-2.Products derived from a cyclopropeno lactone of type A could not be detected.