The butterfly effect (a small change can have large repercussions): Dissociative electron attachment (DEA) was used to probe the reactivities of purine derivatives. A change of the substituent at the C6 position of adenine strongly affects the ion yield of the closed‐shell dehydrogenated anion (see picture), although the hydrogen loss can be ascribed exclusively to the diametric N9 position.

A new method for the synthesis of fluorinated α-C-glycosides is described. The reactions between highly electrophilic radicals (fluorinated or unfluorinated) and a 2-benzyloxyglucal or galactal provide 2-keto-D-arabino- or 2-keto-D-lyxo-hexopyranosides through an addition/fragmentation process. Sodium borohydride mediated or Meerwein-Ponndorf-Verley (MPV) reduction of these compounds provides α-C-glycosides that feature appropriate anchoring groups for further synthetic elaboration. The presence of CF2 CO2 iPr or CF2 Br groups at the pseudo-anomeric position allows efficient reduction/olefination or Br/Li-exchange/nucleophilic-addition sequences. These transformations open the way for the synthesis of fluorinated C-glycosidic analogues of glycoconjugates.