Collect. Czech. Chem. Commun. 1986, 51, 1119-1126

Reactions of 3-butine-2-methyl-2-ol with isothiocyanates

Peter Kutschy, Milan Dzurilla, Ladislav Kniežo, Juraj Bernát, Ján Imrich, Pavol Kristian and Róbert Nádaskay

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, J. P. Šafárik University, Moyzesova 11, 041 67 Košice


3-Butine-2-methyl-2-ol reacts with isothiocyanates in the presence of sodium hydride in dimethylformamide to give various products depending on structure of the isothiocyanate residue. Isothiocyanates with the NCS group bound to sp2 carbon atom (phenyl, 4-bromophenyl, and styryl isothiocyanates) give the respective 1,3-oxazolidine derivatives. If the NCS group is bound to an sp3-hybridized carbon atom (ethyl and benzyl isothiocyanates), derivatives of 1,3-oxathiolane are formed. Acyl isothiocyanates (benzoyl and 3-phenylpropenoyl isothiocyanates) give products of substitution of the NCS group, viz. 1-butine-3-methyl-3-yl benzoate and 3-phenylpropenoic anhydride.