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An Efficient Preparation of Vinamidinium Hexafluorophosphate Salts

2000; American Chemical Society; Volume: 65; Issue: 15 Linguagem: Inglês

10.1021/jo000159u

1520-6904

Ian W. Davies, Jean-François Marcoux, Jimmy Wu, Michael Palucki, Edward G. Corley, Michael A. Robbins, Nancy N. Tsou, Richard G. Ball, Peter G. Dormer, Robert D. Larsen, Paul J. Reider,

Asymmetric Synthesis and Catalysis

Substituted acetic acids or acetyl chlorides react with phosphorus oxychloride in DMF to yield the vinamidinium salts 3a-j in moderate to excellent recrystallized yields (28-90%). The cations are conveniently isolated as their hexafluorophosphate salts, which are easily handled nonhygroscopic solids. The nitro compound 3l is prepared in 91% yield by nitration of the parent vinamidinium 3k. The X-ray crystal structure is reported for the 2-phenyl isomer 3e and displays minimal overlap of the two pi-systems.