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
Document Type
Article
Publication Date
12-3-2014
Abstract
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.
Publication Title
Tetrahedron Letters
Volume
55
Issue
49
First Page
6643
Last Page
6646
Digital Object Identifier (DOI)
10.1016/j.tetlet.2014.10.071
ISSN
00404039
E-ISSN
18733581
Citation Information
Laali, Jamalian, A., & Zhao, C. (2014). 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. Tetrahedron Letters, 55(49), 6643–6646. https://doi.org/10.1016/j.tetlet.2014.10.071