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

Isothiocyanates. XIV. The preparation and properties of substituted benzyl isothiocyanates

K. Antoš, A. Štullerová, V. Knoppová, and P. Kristián

Department of Organic Chemistry, Slovak Technical University, Bratislava

Abstract: The synthesis of m- and p-substituted benzylisothiocyanates has been described. Due to the sensibility of the starting amines to aerial carbon dioxide, the reaction was carried out under a nitrogen atmosphere. The amine was set free by a stepwise addition of a sodium hydroxide solution, the reaction medium being kept mildly alkaline. The reaction kinetics of glycine additions determined by the spectrophotometric method in the ultraviolet region point to the fact, that the reactivity of various benzylisothiocyanates differs only slightly. The infrared spectra of the synthesized benzylisothiocyanates were studied in the region from 2000 to 2200 cm^-1 . The obtainedNvalues of v_asym. _NCS of the substituted single benzylisothiocyanates give evidence for a good correlation (r = —0.94) between the infrared data and the σ_I  values of individual substituents.

Full paper in Portable Document Format: 195a353.pdf (in Slovak)

Chemical Papers 19 (5) 353–359 (1965)