Treatment of 3-oxo-6-heptenoate esters 1, 2, 4-15 with 4 equiv of Mn(0Ac)3-2H20 and 1 equiv of Cu(0Ac)2-H20 gave salicylate esters 16-29 in yields of 17-78%. Similar treatment with 4 equiv of Mn(0Ac)3-2H20 and excess LiCl gave mixtures of salicylate esters and chlorides such as 45 and 46, which could be converted to the salicylate ester by heating at reflux in acetic acid containing excess LiCl in overall yields of 40-90%. Treatment of a-chloro /3-keto ester 3 with 2 equiv of Mn(0Ac)3-2H20 and 1 equiv of Cu(0Ac)2-H20 gave a mixture of salicylate 17 and methylenecyclohexane 41. Treatment of 5-hydroxy /3-keto esters 51a and 51b with 2 equiv of Mn(0Ac)3-2H20 gave epoxides 53a and 53b in 50% and 30% yield, respectively.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.