ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Isothiocyanates. XIX. The synthesis and infrared spectra of polynuclear aryl methyl isothiocyanates
P. Kristián, E. Závodská, K. Antoš, and Ľ. Drobnica
Department of Organic Chemistry, P. J. Šafárik University,
Abstract: The synthesis and infra-red spectra of aryl-methyl-isothiocyantes viz. 1-isothiocyanato
methylnaphtalene, 9-isothiocyanate methylphenanthrene and 9-isothiocyanate methylanthracene
are reported. The above mentioned compounds were prepared by thiophosgene method from the corresponding amines, with the yield in the range of 35—40 %.
1-Isothiocyanate methylnaphtalene has already been prepared by the rearrangement of
the corresponding thiocyanate. The synthesis of 9-aminomethyl anthracene and 9-aminomethyl
phenanthrene was carried out from the appropriate chloromethyl derivatives,
by the decomposition of their hexaammonium salts. In addition, the procedure for the
preparation of Ar-methylaniline, by the acid hydrolysis of N-methylacetamide in quantitative
yield is described. N-Methylacetanilide was prepared by the methylation of
sodium salt of acetanilide with dimethylsulfate. The infra-red spectra of the studied
isothiocyanates exhibit the absorbtion maxima £asym. NCS in the region for 1900—2200 cm-1.
It could be deduced that f/asym. NCS were shifted to the lower frequencies with the
increasing number of the condensed nuclei.
Full paper in Portable Document Format: 211-2a57.pdf (in Slovak)
Chemical Papers 21 (1-2) 57–64 (1967)