Reaction of Selectfluor (F-TEDA-BF sub(4)) with chloromethylated-DABCO monocation salts (X = BF sub(4), NTf sub(2)) and other nitrogen bases (Et sub(3)N; piperidine; basic ionic liquid); unexpected formation of symmetrical [N-H-N] super(+) trication salts

Selectfluor reacts with N-chloromethylated DABCO monocation BF sub(4) or NTf sub(2) salts in MeCN (rt to 80 degree C) to give symmetrical [N-H-N] super(+) trication salts. The same dimeric adducts are formed via the reaction of Selectfluor with Et sub(3)N, piperidine, or a basic-IL (imidazolium with...

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Bibliographic Details
Published in:Tetrahedron letters 2014-12, Vol.55 (49), p.6643-6646
Main Authors: Laali, Kenneth K, Jamalian, Arezu, Zhao, Chunqing
Format: Article
Language:English
Subjects:
Adducts
Alkaloids
Fluorination
Formations
Ionic liquids
Piperidine
Tethers
Tetrahedrons
Online Access:Get full text
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Description
Summary:Selectfluor reacts with N-chloromethylated DABCO monocation BF sub(4) or NTf sub(2) salts in MeCN (rt to 80 degree C) to give symmetrical [N-H-N] super(+) trication salts. The same dimeric adducts are formed via the reaction of Selectfluor with Et sub(3)N, piperidine, or a basic-IL (imidazolium with an alkyl-piperidine tether). The resulting stable salts were studied by multinuclear NMR, super(15)N/ super(1)H HMBC, electrospray-MS, and by chemical reactivity. This hitherto unreported reactivity behavior contrasts the well documented 'transfer fluorination' by Selectfluor to quinuclidine and the quinuclidinic nitrogen of cinchona alkaloids.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2014.10.071