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2825759 
Journal Article 
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 
Laali, KK; Jamalian, A; Zhao, C 
2014 
1 
Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581 
55 
49 
6643-6646 
WOS:000345820900008 
Selectfluor reacts with N-chloromethylated DABCO monocation BF4 or NTf2 salts in MeCN (rt to 80 degrees 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, N-15/H-1 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. (C) 2014 Elsevier Ltd. All rights reserved. 
Selectfluor; Chloromethylated DABCO monocation; BF4 and NTf2 salts; Symmetrical [N-H-N](+) trication salts; Nitrogen bases; N-15 NMR