ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
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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)

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