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Concave Wrapped Protons: Reagents for Contra‐Thermodynamic Protonations
Author(s) -
Lüning Ulrich,
Müller Michael
Publication year - 1992
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199200801
Subject(s) - nitronate , reagent , chemistry , stereoselectivity , ion , aryl , transition state , medicinal chemistry , organic chemistry , catalysis , alkyl , nitro
Good stereoselectivity in the reprotonation of nitronate ions R 2 C − NO 2 is achieved, if the bis‐ ortho ‐substituted 2‐aryl‐1,10‐phenanthroline 1 is added as a buffer. Both for cyclic and acyclic nitronate ions the reaction proceeds via transition states which lead to a thermodynamically less stable product. R = H, Me, Ph.
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