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Superbase-catalyzed domino 3H-pyrroles synthesis from ketoximes and acetylene: DFT study vs experiment

Research paper by Anton V. Kuzmin, Dmitrii A. Shabalin

Indexed on: 28 Feb '18Published on: 27 Feb '18Published in: Journal of Physical Organic Chemistry



Abstract

Elimination of vinyl alcohol from 5-vinyloxypyrrolines in the presence of superbases (final step of domino 3H-pyrroles synthesis from ketoximes and acetylene) is studied computationally at different levels of theory in DMSO solution (PCM). The sequences of transformations starting from nucleophilic addition of hydroxide ion to carbon-carbon or carbon-nitrogen double bonds are proposed as possible mechanisms. Unusual reactivity of 2,5-dimethylphenyl substituted 5-vinyloxypyrroline is explained within these mechanisms.