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2,5-Disubstituted furan derivatives. III. Rearrangement of furfuryl thiocyanates into isothiocyanates

A. Jurášek and J. Kováč

Slovak Technical University, Bratislava

 

Abstract: cf. CA 61, 14617c. Furfuryl thiocyanate (I), n20D 1.5419, was prepd. by the reaction of alkali thiocyanates with halomethyl derivs. of furan at 5-25°. I was purified twice on a column with activated Al2O3. Triple distn. of the product, 1st at 103-110°/14 mm., then at 103-107°/14 mm., and finally at 106°/14 mm., coursed isomerization of I to furfuryl isothiocyanate, n20D 1.5630. After heating 6 hrs. on a boiling water bath, a mixt. of 5-nitrofurfuryl iodide and NH4CNS in EtOH yielded yellow crystals of 5-nitrofurfuryl thiocyanate, m. 93.5°. It was detd. that the esters of 5-thiocyanatomethylpyromucic acid, starting with the Et ester, are rearranged at the distn. temps., into isothiocyanates. Only Me ester distrils unchanged. The greater the mol. wt. the higher the formation of the isothiocyanate derivs. The ir absorption spectra of the rearranged products in the area 2300-1900 cm-1 are given.

Full paper in Portable Document Format: 1911a840.pdf (in Slovak)

 

Chemical Papers 19 (11) 840–845 (1965)

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