Perfluoropropionic anhydride

To be able to determine nicotine in sub-picomole quantities Neelakantan and Kostenbauer11 used an electron-capture detector in connection with derivatization of nicotine Nicotine was hydrogenated catalytically to yield N-methyl-4-(3 -piperidyl)-n-butylamine (= octahydro-nicotine), the two secondary amino-functions of which were treated with perfluoropropionic anhydride to give the di-pentafluoropropionyl octahydronicotine. The perfluoropropionyl derivative of octahydronicotine provides an electron capture derivative which represents a means of detecting nicotine in amounts of approximately l/100th of the minimum quantity of nicotine that is detectable by FID. 

Much of the data in Table 27 have been obtained using perfluorodiethyl ketone as the radical source. More recently, Chamberlain and Whittle [331] have shown that the photolysis (X — 2540 A) of perfluoropropionic anhydride is an excellent clean source of C2 F5 radicals. 

Methyl-2-pentafluoroethyl-J -5-oxazolone (as a mixture with perfluoropropionic acid from its prepn. with perfluoropropionic anhydride and DL-alanine) added dropwise with stirring and ice-cooling to a mixture of HBr-glacial acetic acid and ethyl mercaptan, well shaken, and allowed to stand 1 hr. in the ice-bath 2,2,3,3,3-pentafluoro-l-ethylthiopropylamine hydrobromide. Y 79%. F. e. s. F. Weygand, W. Steglidi, and W. Oettmeier, B. 103, 818 (1970). 

In another two-step NNCC+CC strategy, acylation of hydrazones 1045 with perfluoropropionic anhydride led to the formation of 1046, which underwent cyclization to pyridazines 1047 upon heating with silica gel (Scheme 223) [627],... 

A recent study has further proven the applicability of gas-phase reactions to functional groups at the monolayer surface. Alcohol terminal groups were quantitatively converted to trifluoroacetates by exposure to the vapours of trifluoroacetic anhydride (equation 7). Reaction with perfluoropropionic and perfluorobutyric anhydrides proceeded similarly, but with ca 80% yield (XPS). Very high contact angles (>120°) of perfluoro-terminated layers proved the formation of esters333. 

---