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Structural NMR Investigations on Allyllithium Compounds
Author(s) -
Balzer Hartmut,
Berger Stefan
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250329
Subject(s) - chemistry , moiety , nuclear magnetic resonance spectroscopy , lithium atom , ring (chemistry) , allylic rearrangement , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , crystallography , nuclear overhauser effect , lithium (medication) , organic chemistry , medicine , ion , ionization , endocrinology , catalysis
Four differently substituted phenylallyllithium compounds Li · 2 have been investigated by dynamic 1 H‐ and 13 C‐NMR, NOESY and HOESY spectroscopy. It is shown that a considerable barrier of rotation (ca. 40 kJ/mol) between the phenyl and the allyl moiety exists which is only slightly affected by the addition of TMEDA. The lithium atom prefers a bridged position with respect to the allylic part in solution and has HOESY contacts to the ortho hydrogen atoms of the aromatic ring.