James M. Bobbitt
Chemical & Engineering News (19 Jan 1999) Vol. 77, No. 29, p. 6.
Last December, I published a paper describing the synthesis and reactions of two oxoammonium salts, 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate and tetrafluoroborate [J. Org. Chem., 63, 9367 (1998)]. These salts are non-heavy metal, colorimetric oxidizing agents for the conversion of alcohols to aldehydes or ketones in essentially quantitative yields with minimal work-up procedures.
Almost all of the experimental procedures described in the article were related to the perchlorate, although the oxidants seemed to have nearly identical properties. The air-dried perchlorate has been used for roughly six years and was reported to be quite stable. Unfortunately, when an 8-g sample was dried over P2O5 under high vacuum at 55 °C, it detonated. Though the damage was minimal, the explosion was rather violent.
Those who have prepared a supply of the perchlorate are encouraged to destroy it by dissolving it in water and reducing it with ethanol and NaHCO3 as described in the paper.
As far as it is known, the tetrafluoroborate is stable up to at least 95 °C under the conditions described above and has the same outstanding oxidizing properties as the perchlorate.
This page last revised December 26, 2006