Aminodefluorination of 2-X-pentafluoro-1,4-naphthoquinones (X = (NHBu)-Bu-n, NEt2, and OMe)

作者：Troshkova Nadezhda M; Goryunov Leonid I; Gatilov Yurij V; Nevinsky Georgy A; Shteingarts Vitalij D^*

来源：Journal of Fluorine Chemistry, 2010, 131(1): 70-77.

DOI：10.1016/j.jfluchem.2009.10.007

• Hexafluoro-1,4-naphthoquinone
• 2-Alkylaminopentafluoro-1,4-naphthoquinone
• Aminodefluorination
• Nucleophilic substitution
• Regioselectivity

Aminodefluorination of 2-n-butylamino- and 2-diethylaminopentafluoro-1,4-naphthoquinone by alkylamines (HNRR2)-R-1 ((NRR2)-R-1 = NHEt, (NHBu)-Bu-n and NEt2) occurs at the 6- or 8-position and further, accordingly, at the 8- or at one of the 5- and 6-sites. The isomer ratio changes significantly in favor of a beta-replacement product with solvent variation in the sequence: toluene < 1,4-dioxane < DMSO. n-Butylaminodefluorination of 2-methoxypentafluoro-1,4-naphthoquinone gives mixtures of fluorine substitution products both on the benzene and quinone rings.

• 出版日期2010-1