77894-23-6Relevant academic research and scientific papers
SELECTIVE FLUORINATION ON TERTIARY CARBON-HYDROGEN SINGLE BONDS IN THE ALIPHATIC SERIES
Gal, Chava,Ben-Shosan, Giora,Rozen, Shlomo
, p. 5067 - 5070 (1980)
Fluorine acts as an electrophile and, as such, reacts with remote and unactivated tertiary hydrogens in aliphatic alcohols and acids, resulting in the corresponding fluorine derivatives.
Selective Substitution of Aliphatic Remote Tetriary Hydrogens by Fluorine
Rozen, Shlomo,Gal, Chava
, p. 4928 - 4933 (2007/10/02)
Substitution of saturated hydrogens is a very desirable but difficult task.Elemental fluorine under suitable conditions, including a polar solvent and low temperatures, acts as an electrophile strong enough to react with saturated tetriary CH bonds of various aliphatic compounds.The regioselectivity and the readiness of the hydrogen substitution by fluorine are functions of the p-orbital contribution to the bond, in agreement with the electrophilic nature of the reaction.Apart from branched paraffins, oxygen- as well as nitrogen-containing aliphatic molecules can participate in the reaction, and various protecting groups and their effectiveness were examined.The role of the electron-withdrawing group on the selectivity was also evaluated.
