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Isothiocyanates. XII. Preparation and infrared spectra of m- and p-acyloxyphenyl isothiocyanates

P. Kristián, J. Antoš, and Š. Kováč

Slovak Technical University, Bratislava

Abstract: cf. CA 59, 14742a. A new method for a direct acylation of m- and p-hydroxyphenyl isothiocyanates (0.1 mole) with various acyl halides (0.1 mole) was described. The following isothiocyanates were prepd.: m-acetoxyphenyl, b0.5 103°, n20D 1.6129, 60%; p-acetoxyphenyl, m. 34° (petr. ether), 72%, m-butyryloxyphenyl, n20D = 1.5855, 55%; p-butyryloxyphenyl, m. 23°, 69%; m-benzoyloxyphenyl, m. 61°, 41.5%; p-benzyloxyphenyl, m. 66°, 64.5%; m-nicotinoyloxyphenyl, m. 72°, 35%; and p-nicotinoyloxyphenyl, m. 82°, 47%. The infrared absorption spectra were measured in the area 3600-400 cm^-1 on a UR 10 spectrophotometer. m-Benzoyl- and m-nicotinoyloxyphenyl isothiocyanates have absorption bands νasym.NCS shifted to lower wavelengths (∼2070 cm^-1), as compared with the others (2110 cm^-1). In acyloxyphenyl isothicyanates with aliphatic acyl groups, the CO vibration bands are shifted to higher wavelengths (∼1770 cm^-1), as compared with those contg. aromatic acyl groups (∼1750 cm^-1).

Full paper in Portable Document Format: 1710-11a747.pdf (in Slovak)

Chemical Papers 17 (10-11) 747–756 (1963)