649-16-1Relevant academic research and scientific papers
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, Kenneth K.,Jamalian, Arezu,Zhao, Chunqing
, p. 6643 - 6646 (2015/01/09)
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.
N-Halogeno compounds. Part 20. Vicarious electrophilic fluorodemethylation of 1,3,5-trimethoxybenzene and 2,4,6-trimethoxytoluene with 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor reagent F-TEDA-BF4
Banks, R. Eric,Besheesh, Mohamed K.,Gorski, Romuald W.,Lawrence, Nicholas J.,Taylor, Amanda J.
, p. 129 - 133 (2007/10/03)
Treatment of 1,3,5-trimethoxybenzene with one molar equivalence of 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4) under mild conditions (-40 to +20°C) in acetonitrile gave mainly 2-fluoro-1,3,5-trim
