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On the Roles of Protic Solvents in Imidazolidinone‐Catalyzed Transformations
Author(s) -
Brazier John B.,
Jones Kevin M.,
Platts James A.,
Tomkinson Nicholas C. O.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201005892
Subject(s) - iminium , cycloaddition , chemistry , solvent , adduct , catalysis , ion , solvent effects , organic chemistry , combinatorial chemistry , photochemistry
Step by step : The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone‐catalyzed Diels–Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (step 1), the Diels–Alder cycloaddition is reversible (step 2), and the solvent intercepts the iminium ion adduct (step 3).
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