Reactions in Ethyl Acetate | Reactions in Dichloromethane with Complete Evaporation | Reactions in Dichloromethane with Cooling | ||||
---|---|---|---|---|---|---|
A | B | C | D | E | F | |
Initial IF | 1 mg | 2 mg | 1 mg | 2 mg | 1 mg | 2 mg |
% Recovery | 108.6 | 100.7 | 35.6 | 26.3 | 81.1 | 87.5 |
% IF | 0 | 0 | 3.0 | 3.7 | 36.2 | 62.8 |
0 | 0 | |||||
% Trifluoroacetylated IF (compound VI) | 98.2 | 95.2 | 0.9 | 0.8 | 2.9 | 2.4 |
CF3CONH(CH2)2Cl (compound VII) | 0 | 0 | 9.5 | 10.1 | 0.4 | 0.3 |
% Other trifluoroacetylated compounds (unidentified) | 10.4 | 5.5 | 23.8 | 13.5 | 41.9 | 22.1 |
IF (1 or 2 mg), dissolved in 1,200 μl of ethyl acetate or dichloromethane, was derivatized with 1,200 μl TFAA. Indicated values are the means of two separate experiments, except for the percentage of IF in experiments C and D. 31P NMR was used solely to assay underivatized IF. 19F NMR was used to assay the fluorinated compounds VI, VII, and unidentified products (assuming they were all monotrifluoroacetylated).