Reaction of Selectfluor (F-TEDA-BF4) with chloromethylated-DABCO monocation salts (X=BF4, NTf2) and other nitrogen bases (Et3N; piperidine; basic ionic liquid); unexpected formation of symmetrical [N−H−N]+ trication salts

[Display omitted] Selectfluor reacts with N-chloromethylated DABCO monocation BF4 or NTf2 salts in MeCN (rt to 80°C) to give symmetrical [N−H−N]+ trication salts. The same dimeric adducts are formed via the reaction of Selectfluor with Et3N, piperidine, or a basic-IL (imidazolium with an alkyl-piper...

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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:
15N NMR
BF4 and NTf2 salts
Chloromethylated DABCO monocation
Nitrogen bases
Selectfluor
Symmetrical [N−H−N]+ trication salts
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Description
Summary:[Display omitted] Selectfluor reacts with N-chloromethylated DABCO monocation BF4 or NTf2 salts in MeCN (rt to 80°C) to give symmetrical [N−H−N]+ trication salts. The same dimeric adducts are formed via the reaction of Selectfluor with Et3N, piperidine, or a basic-IL (imidazolium with an alkyl-piperidine tether). The resulting stable salts were studied by multinuclear NMR, 15N/1H 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
1873-3581
DOI:10.1016/j.tetlet.2014.10.071