The invention of new radical chain reactions. Part 12. Improved methods for the addition of carbon radicals to substituted allylic groups

Abstract

Reagents for the allylation of carbon radicals derived from the esters (mixed anydrides) of N-hydroxy-2-thiopyridone have been investigated. Because of competition between the background reaction of decarboxylative rearrangement and the desired allylation process, conventional allylation reagents give moderate yields of the desired adducts. Improved yields are secured if the β-position bears an electron withdrawing group. A concerted addition and elimination process can be postulated.