ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Isothiocyanates. XX. Preparation of the principle diarylmethyl isothiocyanates with a condensed aromatic nucleus

J. Kalamár, K. Bencze, and P. Křenek

Slovak Technical University, Bratislava

Abstract: cf. CA 67: 63558s. The synthesis of benzyhdryl (I), phenyl-1-naphthylmethyl (II), and phenyl-2-naphthylmethyl isothiocyanate (III), their intermediary products and their uv and ir spectra were described. These isocyanates were prepd. from ketones which were changed into amines according to a modified Leuckart-Wallach reaction; amines condensed with CSCl2 at 30° in C₂H₄Cl₂ and H2O in the presence of CaCO₃. A procedure was developed for the purification of phenyl naphthyl ketones by crystn. from alc. and n-heptane. I, m. 60°, was prepd. from benzophenone via benzhydrylamine, II, m. 77.5°, from naphthalene and BzCl via phenyl 1-naphthyl ketone and phenyl(1-naphthyl)methylamine, and III, m. 65°, by the 4-step reaction from tetrahydronaphthalene and BzCl via phenyl tetrahydro-2-naphthyl ketone and phenyl 2-naphthyl ketone, Uv spectra of the synthesized products measured in purified n-heptane, were studied at 195 to 400 mμ and the effect of the functional groups NH₂ and NCS on shifting of the frequencies was detd. Ir spectra show that I in CCl₄ has ν 2060 cm.^-1, II at 2052 cm.^-1 with 2 inflection points at 2104 and 2078 cm.^-1 and III has ν 2069 and 2133 cm.^-1

Full paper in Portable Document Format: 215a350.pdf (in Slovak)

Chemical Papers 21 (5) 350–358 (1967)