left 1.4 g (75%) of triphenylphosphine oxide. The pentane solution was evaporated. The residue, 2.9 g of orange oil, exhibited a small peak at 4.71 µ in the ir; there was a strong pyridine-like odor apparent. The oil was taken up in benzene and treated with anhydrous hydrogen chloride. Solvent was evaporated and the residue was washed with cold methanol. There remained 1.5 g (52%) of crude 14, mp 175°. Recrystallization from ethyl acetate raised the melting point to 185-189°; ir NH peak at 2.96 µ, strongest peak at 6.26 µ; nmr multiplet at 2.5-3.4 (20) and a broad singlet at 4.7 (0.8).
Takeshima for their kind advice. Thanks are also due to Dr. Haruo Homma and his staff for their microanalyses, to Mr. Jun Uzawa for his measurements of the nmr spectra, and to Mr. Hironori Ogawa for his measurements of the ir spectra.
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