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Mechanistic Insights and Safety Evaluation of the Ritter Reaction Utilizing tert-Butyl Acetate as the tert-Butyl Cation Source

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journal contribution
posted on 21.12.2012, 00:00 by Scott W. Roberts, Stephen M. Shaw, Jacqueline E. Milne, Dawn E. Cohen, Justin T. Tvetan, Joseph Tomaskevitch, Oliver R. Thiel
The Ritter reaction utilizing tert-butyl acetate as the tert-butyl cation source was investigated by in situ FTIR and calorimetry under various reaction conditions. It was established that, when a batch mode reaction in acetic acid was performed, minimal isobutylene was evolved into the headspace, thereby avoiding pressurization of the reaction vessel. The safety of these conditions is due to the equilibrium of isobutylene and acetic acid with tert-butyl acetate. In addition, the observation of acetic anhydride provided insight into the role of acetic acid in the mechanistic pathway.