Ortho-Coordinated Acylation on Phenol Systems

Article abstract of DOI:10.1021/jo00301a031

The ortho-coordinated acylation of phenol salts reported in recent synthetic applications has been extensively investigated.The data obtained support the hypothesis that formation of an organized complex between the phenol salts and the acylating agents may strongly influence the reaction pathway, depending on the nature of the specific cation, phenol, and acyl chloride involved in the process.The structural factors which control the formation of the reacting complex 3 have been extensively investigated; the results obtained allow us to discuss the possibilities and limitations of this methodology in selective o-acylphenol synthesis.The present methodology is the procedure of choice for ortho-functionalization of phenols with electrophilic reagents such as phosgene, oxaloyl chlorides, polyunsaturated acid chlorides, phthalic dichlorides, and, in general, acid chlorides α-functionalized with an electron-withdrawing group.