was also isolated which had the following spectroscopic properties: ir spectrum (CH2CI2) showed absorptions characteristic of sulfinates, 1128 (s) and 952 (s), and of sulfinamides, 1085 (s), 1057 (s), 1016 (m), 868 (m); nmr (CDC13) 1,39 (d, 3, J = 7.0 Hz), 2.38 (s, 3), 2.41 (s, 3), 3.70 (quintet, 1,7 = 7.0 Hz), 5.24 (d, 1,7 = 7.0 Hz), 7.2-7.61 (m, 13). This material was presumably /-ephedrine 0-(p-toluenesulfinyl)-p-toluenesulfinamide. Methylmagnesium Bromide. A solution of methylmagnesium bromide (based on 40 mg (1.64 mmol) of magnesium) and 190 mg of (1.64 mmol) TMEDA in 15 ml THE was added dropwise with stirring to a soluton of 250 mg (0.82 mmol) of (i?)-/-ephedrine ptoluenesulfinate [(7?)-7a] in 20 ml of THE at -25°. The reaction was allowed to continue for 1.5 hr. The usual work-up followed by thick-layer chromatography using 20% methylene chloride and acetonitrile solvent mixture as the eluent afforded 63 mg (51 %) of pure methyl p-tolyl sulfoxide: mp 75-76°(lit.3•36 mp 74-75.5°); M25546 +182.5°(c 2.13, acetone) (lit.36 [a]2S546 +180.5°(c 1.61, acetone)). No /-ephedrine p-toluenesulfinamide (3a) could be detected or isolated.A similar result was obtained when this reaction was carried out in the absence of TMEDA.Acknowledgment. The authors thank the Petroleum Research Fund, administered by the American Chemical Society, the Research Corporation for a Frederick Gardner Cottrell Grant, the Merck Fund for an award, and the Research Foundation of SUNY for partial support of this work. We thank Professor J. J. Tufariello for helpful discussions.
