Selectivity of nucleophilic addition to and substitution at isothiocyanatocarbonyl group. Reactions of 4-pentinoyl-and 2-(2-propinyl)-4-pentinoyl isothiocyanate with …

P Kutschy, P Kristian, M Dzurilla, D Koščík…

Index: Kutschy, Peter; Kristian, Pavol; Dzurilla, Milan; Koscik, Dusan; Nadaskay, Robert Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 4 p. 995 - 1005

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Abstract

Abstract 4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N= C= S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides. The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl ...