A fast radical chain mechanism in the polyfluoroalkoxylation of aromatics through NO2 group displacement. Mechanistic and theoretical studies

…, À González-Lafont, JM Lluch, J Marquet

Index: Tejero, Ismael; Huertas, Imma; Gonzalez-Lafont, Angels; Lluch, Jose M.; Marquet, Jordi Journal of Organic Chemistry, 2005 , vol. 70, # 5 p. 1718 - 1727

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Citation Number: 21

Abstract

Introduction of polyfluoroalkoxy and polyfluoroalkylthio substituents in aromatic rings can be achieved with mild conditions and short times thorough reaction of concentrated solutions of dinitrobenzenes in DMF with polyfluoro alcohols and polyfluoro thiols in moderate excess, in the presence of excess tetrabutylammonium fluoride as a base. Mechanistic studies suggest that under these conditions a fast radical chain mechanism operates. This mechanism is ...

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N-Arylpiperazinyl-N'-propylamino Derivatives of Heteroaryl A...

[Elworthy, Todd R.; Ford, Anthony P. D. W.; Bantle, Gary W.; Morgans Jr., David J.; Ozer, Rachel S.; Palmer, Wylie S.; Repke, David B.; Romero, Magarita; Sandoval, Leticia; Sjogren, Eric B.; Talamas, Francisco X.; Vazquez, Alfredo; Wu, Helen; Arredondo, Nicolas F.; Blue Jr., David R.; DeSousa, Andrea; Gross, Lisa M.; Kava, M. Shannon; Lesnick, John D.; Vimont, Rachel L.; Williams, Timothy J.; Zhu, Quan-Ming; Pfister, Juerg R.; Clarke, David E. Journal of Medicinal Chemistry, 1997 , vol. 40, # 17 p. 2674 - 2687]

Aromatic fluoroalkoxylation via direct aromatic nucleophilic...

[Idoux, John P.; Gupton, John T.; McCurry, Cynthia K.; Crews, A. Donald; Jurss, Cindy D.; et al. Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3771 - 3773]