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

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, Košice

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)