2627-94-3Relevant articles and documents
Barton et al.
, p. 804 (1968)
Synthesis, Properties, and Reactivity of N,N'-Difluorobipyridinium and Related Salts and Their Applications as Reactive and Easy-To-Handle Electrophilic Fluorinating Agents with High Effective Fluorine Content
Umemoto, Teruo,Nagayoshi, Masayuki,Adachi, Kenji,Tomizawa, Ginjiro
, p. 3379 - 3385 (2007/10/03)
N,N′-Difluoro-2,2′-, -2,4′-, -3,3′-, -4,4′-bipyridinium and substituted N,N′-difluoro-2,2′-bipyridinmm bis(triflates), bis(tetrafluoroborates), bis(hexafluorophosphates), and bis(hexafluoroantimonates) 1-9 were synthesized in high yields by the direct fluorination of a mixture of a bipyridyl and a Lewis acid, a Br?nsted acid, or the alkali metal salt of an acid. The higher homologues, trimer 10 and polymer 11, were also synthesized. Unsubstituted or electron-donating group-substituted N,N′- difluorobipyridinium salts are stable nonhygroscopic crystals, while the electron-withdrawing group- substituted N,N′-diflurobipyridinium salts 3, 5, and 6 are moisture-sensitive crystals. Hydrolysis of 1b in boiling water gave 3,3′-dihydroxy-2,2′-bipyridyl. The reactivity determination indicated that the fluorinating capability decreased in the order 2,2′- ? 2,4' > 3,3′- ≈ 4,4′-isomer ? N-fluoropyridinium salt and that the two N-F moieties in a molecule were effective for fluorination. This fluorination occurred in a step-by-step manner, and the reactivity difference between the first and second fluorinations was very small. N,N′-Difluoro-2,2′-bipyridinium bis(tetrafluoroborate) (1b) is thus shown to be a highly reactive and easy-to-handle electrophilic fluorinating agent with the high effective fluorine content (103.3 g/kg) for preparing many fluoro organic compounds.
1-Alkyl-4-fluoro-1,4-diazoniabicyclooctane Salts: a Novel Family of Electrophilic Fluorinating Agents
Banks, R. Eric,Mohialdin-Khaffaf, Suad N.,Lai, G. Sankar,Sharif, Iqbal,Syvret, Robert G.
, p. 595 - 596 (2007/10/02)
Members of a new series of solid, easily handled, storable, transportable, commercially viable, site-selective electrophilic fluorinating agents of the +N-F class (tradenamed Selectfluor reagents) have been synthesized via direct fluorination of monoquaternary salts of 1,4-diazabicyclooctane.