We have developed an improved synthesis of the oxidizing salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate. This new method not only improves the overall yield but also reduces the total number of steps in its preparation. Moreover, the entire process is now conducted entirely in water further enhancing the �green chemistry� profile of this reagent. We have recently explored the use of this oxidizing agent in the oxidation of ketones, in particular cycloheptanone to cycloheptenone. We have observed the formation of the desired a, �-unsaturated product, accompanied by the formation of 1,2-diones via an a-oxidation mechanism. Our current efforts focus on the development of a method to direct this process either towards sole dehydrogenation or a-oxidation.

Improved preparation of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (“Bobbitt's Salt”) and its use in the dehydrogenation of ketones

245th National Meeting (2013)

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