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Superbase‐catalyzed domino 3 H ‐pyrroles synthesis from ketoximes and acetylene: DFT study vs experiment
Author(s) -
Kuzmin Anton V.,
Shabalin Dmitrii A.
Publication year - 2018
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3829
Subject(s) - chemistry , superbase , acetylene , domino , reactivity (psychology) , nucleophile , catalysis , nucleophilic addition , carbon fibers , hydroxide , medicinal chemistry , organic chemistry , medicine , materials science , alternative medicine , pathology , composite number , composite material
Abstract Elimination of vinyl alcohol from 5‐vinyloxypyrrolines in the presence of superbases (final step of domino 3 H ‐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.