2655The elution order for the toluonitriles was ortho < meta < para and for the dimethylbenzonitriles 2,5 < 2,4 < 3,4.
RegistryNo. o-Toluonitrile, 529-19-1; m-toluonitrile, 620-22-4; p-toluonitrile, 104-85-8; 2,4-dimethylbenzonitrile, 21789-36-6; 2,5-dimethylbenzonitrile, 13730-09-1; 3,4-dimethylbenzonitrile, 22884-95-3. (12) Lohaus, G. The presence of a ligating group, e.g., OH, C02Me, C=O, or OMe, on an olefinic substrate is shown to direct the attack of the hydrogenation catalyst [Ir(cod)(PCy~)(C~H~N)]PFs/H2/CHzClz from the face of the molecule containing the directing group. Isomerization is a minor side reaction in the cases studied. The origin of this effect is discussed and a model intermediate isolated. (1) Kabuki, T.; Sharpless, K. B. J. Am. Chem. SOC. 1980,102,5974. (2) Thompson, H. W.; Naipawer, R. E. J. Am. Chem. SOC. 1973,95, 6379 and references therein.