[3794-64-7] · C4AgF7O2 · Silver(I) Heptafluorobutanoate · (MW 320.91)
(decomposition of 3-diazocamphor;2 NMR shift reagent)
Physical Data: mp 292-294 °C.
Solubility: no readily available data, but probably soluble in a range of solvents, e.g. CHCl3, CH2Cl2, MeCN, alcohol, THF.
Form Supplied in: white powder; widely available.
Handling, Storage, and Precautions: handle in a fume hood with rubber gloves and safety glasses; avoid skin contact and inhalation. Store in a tight container in a cool place. Light sensitive. Severe eye irritant with an obnoxious smell. The toxicology of this compound has not been fully evaluated.
Little published work has appeared describing the use of this compound as a reagent since the work reviewed in Fieser and Fieser1 on the AgOCOC3F7-assisted decomposition of 3-diazocamphor and its 4-methyl analog, via a carbene intermediate, to the corresponding tricyclanone (eq 1).2 The reaction also occurs with Silver(I) Tetrafluoroborate at 0 °C but no other silver salts have been evaluated.
The reagent has also been used in combination with the lanthanide agent Ln([2H9]fod)3 as an NMR shift reagent for alkenes.3
Duncan R. Rae
Organon Laboratories, Motherwell, UK