Prototropic rearrangement of 2-propynyl (methyl) amino, 2-propynyloxy, and 2-propynylsulfanyl derivatives of hetarenes under conditions of phase-transfer catalysis: …

…, M Fleisher, E Abele, Y Popelis, E Lukevits

Index: Rubina; Fleisher; Abele; Popelis; Lukevits Russian Journal of Organic Chemistry, 2003 , vol. 39, # 7 p. 963 - 967

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Citation Number: 4

Abstract

Abstract 2-Propynyl derivatives of N-methylaniline, phenol, benzenethiol, 2-pyridinethiol, 2- pyrimidinethiol, and 1, 3-benzoxazole-2-thiol were synthesized. Under conditions of phase- transfer catalysis, phenyl 2-propynyl sulfide is converted into allenyl phenyl sulfide and phenyl 1-propynyl sulfide. The rearrangement mechanism was studied by the AM1 quantum- chemical method.