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Phenylsodium Compounds with η 3 ‐Allyl or η 6 ‐Phenyl Coordination
Author(s) -
Corbelin Siegfried,
Kopf Jürgen,
Lorenzen Nis Peter,
Weiss Erwin
Publication year - 1991
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.199108251
Subject(s) - carbanion , steric effects , chemistry , ion , ring (chemistry) , medicinal chemistry , stereochemistry , crystallography , organic chemistry
In spite of the identical negative charge available , phenyl‐substituted allyl anions can be coordinated differently by counter ions. Thus the Na(pmdta) ⊕ (pmdta = pentamethyldiethylenetriamine) ion coordinates in a η 3 manner to the allyl system in 1 , but in a η 6 manner to the phenyl ring in 2 . Apparently the energy surface for the migration of the cation over the planar carbanion in 2 contains no large energy barriers and for steric reasons the Na(pmta) ⊕ ion avoids coordinating with the allyl system of the cyclohexenyl unit.