Factors controlling the fate of radical ipso intermediates. Homolytic alkylation of furan derivatives

Abstract

Radical ipsoσ-complex intermediates have been observed to lead also towards products other than those of ipso substitution; from the reaction of 1-adamantyl radicals with 5-nitro-2-methoxycarbonyl-furan and 5-nitrofuran-2-carbaldehyde, products have been isolated which demonstrate that these intermediates lead to the elimination of a group from a substituent remote from the ipso position and to the coupling with other radicals.