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Exclusive β‐Substitution in the Reaction of Octafluoronaphthalene with Secondary Amines
Author(s) -
Sorokin Vladimir I.,
Ozeryanskii Valery A.,
Pozharskii Alexander F.
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300570
Subject(s) - chemistry , dimethylamine , piperidine , pyrrolidine , fluorine , naphthalene , medicinal chemistry , solvent , ethylene , crystal structure , substitution reaction , organic chemistry , catalysis
The reaction between octafluoronaphthalene and dimethylamine, pyrrolidine or piperidine in DMF, dimethyl(ethylene)urea (DMEU) or without solvent leads to the exclusive substitution of β‐fluorine atoms giving naphthalene derivatives with four NR 2 groups. This was proved by 19 F NMR of the products and a crystal structure determination for 1,4,5,8‐tetrafluoro‐2,3,6,7‐tetrakis(piperidin‐1‐yl)naphthalene. The main feature of the reaction in DMF was a transamidation process. The remaining four fluorine atoms in the synthesised tetraamines could be smoothly replaced by reduction with LiAlH 4 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)