Taming halonium metathesis

• Published in: International journal of mass spectrometry Vol. 222; no. 1; pp. 451 - 463
• Main Authors: Leblanc, Danielle, Kong, Jennie, Mayer, Philip S., Morton, Thomas Hellman
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 2003; Elsevier
• Subjects: Allylic cation; Cyclopentadienyl cation; Hammond postulate; Ion–molecule reaction; Monofluorinated carbocation; Unsaturated ketone; Cyclopentadienyl cation; Allylic cation; Hammond postulate; Unsaturated ketone; Ion–molecule reaction; Monofluorinated carbocation

The halonium metathesis reaction of ketones and aldehydes,  C O+ XF +→ C F ++ X O is difficult to harness for three reasons: (1) the interchange of F + for O is so exothermic that the CF + product ion often decomposes further; (2) the adduct of XF + to the carbonyl oxygen frequently undergoes...