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

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