27248-14-2Relevant academic research and scientific papers
SELECTIVITY OF NUCLEOPHILIC ADDITION TO AND SUBSTITUTION AT ISOTHIOCYANATOCARBONYL GROUP. REACTIONS OF 4-PENTINOYL- AND 2-(2-PROPINYL)-4-PENTINOYL ISOTHIOCYANATE WITH AMINES AND METHANOL
Kutschy, Peter,Kristian, Pavol,Dzurilla, Milan,Koscik, Dusan,Nadaskay, Robert
, p. 995 - 1005 (2007/10/02)
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 group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureasonly.Both isothiocyanates afford with methanol as a nucleophile axclusively the corresponding O-methyl monothiocarbamates.
