Three novel, easily scalable methods for the synthesis of pentafluorosulfanyldifluoroacetic acid � SF5CF2C(O)OH � will be described. Reactions of its acid chloride with amines and alcohols led to a small library of fifteen amides and five esters, respectively. The reaction of the acid chloride with phenylmagnesium bromide gave the corresponding acetophenone. Pentafluorosulfanyldifluoroacetonitrile was obtained from pentafluorosulfanyldifluoroacetamide by dehydration with diphosphorus pentoxide. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/241nm/uploads/71486_acs2011.jpg' alt='' /> A new thermal synthesis of trifluoronitromethane � CF3NO2 � has been discovered from the direct thermal reaction between CF3I and nitrogen dioxide at 200 �C. The increased reaction temperature has allowed for the limitation due to the nitrogen dioxide/dinitrogen tetroxide equilibrium [1] to be overcome, whereby 100-gram quantities of CF3NO2 can be prepared in a single reaction. A new purification method was also developed for the larger quantities of CF3NO2, and CF3NO2was found to be stable to almost 300 �C by accelerating rate calorimetry (ARC).These and other advances in SF5- and CF3-chemistry will be presented.[1] Hauptfleisch, J. O.; Hennek, M. D.; Waterfeld, A.; Fernandez, R. E.; Thrasher, J. S. J. Fluorine Chem. 2012, 133, 72-76.

Recent advances in pentafluorosulfanyl, SF5, and trifluoromethyl, CF3, substituent group chemistry

248th National Meeting (2014)

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