STRUCTURAL STUDIES OF INTERMEDIATES IN A NOVEL SYNTHESIS OF ARYLOXYPROPIONONITRILES. J. Ellena^1,3, G. Punte¹, J.C. Autino², G.P. Romanelli² and A.E. Goeta⁴. ¹PROFIMO. Depto. de Física, Facultad de Ciencias Exactas, UNLP, Argentina, ²LADECOM, Laboratorio de Estudio de Compuestos Orgánicos, Facultad de Cs. Exactas, UNLP, Argentina, ³Facultad de Ingeniería, UNLP, Argentina, ⁴Durham Chemical Crystallography Group, Chemistry Department, University of Durham, UK.

3-Aryloxypropiononitriles are important synthetic intermediates for compounds of biopharmacological and technological uses, such as enzymatic inhibitors, antijuvenile hormones for plague control, biocides, useful polymers, compounds used in the leather industry, etc. A novel synthesis of 3-aryloxypropiononitriles, avoiding the use of contaminants, has proved to give good yields for small substituents[1]. The compounds 2- and 4-(2-bromoethoxy)diphenylmethanes (I and II respectively) have been synthesized as part of a general study on the goodness of the synthetic method to handle bulky substituents. No significant changes in the crystal structures of I and II have been observed in going from R.T. to 150K. The molecular conformation of I and II in solid state, obtained from single crystal X-ray difractometric data at low temperature, are compared. The observed differences are analyzed and the conclusions correlated with solution R.T. ¹H and ¹³C nmr data. Variations in the m.p. as a function of the substituents position are analyzed in terms of the different molecular packing.

[1] A.A. Vitale, G.P. Romanelli, J.C. Autino and A. B. Pomilio. J. Chem. Res. (S), 1993, 386-387.Å