Tetrahedron Letters p. 3465 - 3468 (1998)
Update date:2022-08-11
Topics:
Hannak, Renate B.
Rojas, Christian M.
A C-shaped, bifunctional host with a highly preorganized cleft was used as a host system to investigate the sources of catalysis in the base-promoted conversion of 5-nitrobenzisoxazole to 2-cyano-5-nitrophenolate. Kinetic studies with compounds that partly conserve structural elements of the host suggest that π-stacking interactions and solvation effects mainly contribute to the observed rate acceleration of the host compared to the acetate promoted reaction.
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