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Bicyclo[3.2.1]octa‐2,6‐dienylkalium. Synthese aus dem Dien und 13 C‐NMR‐Spektrum
Author(s) -
Köhler Frank H.,
Hertkorn Norbert
Publication year - 1983
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.19831160925
Subject(s) - chemistry , bicyclic molecule , allylic rearrangement , carbon 13 nmr , stereochemistry , chemical shift , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , catalysis
Bicyclo[3.2.1]octa‐2,6‐dienylpotassium. Synthesis from the Diene and 13 C NMR Spectrum Bicyclo[3.2.1]octa‐2,6‐dienylpotassium ( 2 ) has been obtained as a lemon‐coloured powder by treating bicyclo[3.2.1]octa‐2,6‐diene ( 1 ) with an excess of n ‐butyllithium/potassium tert ‐butoxide in THF. The 13 C NMR shifts show that homohyperconjugation in 2 is small. However, a charge transfer from the allylic to the olefinic part is clearly indicated by high field shifts of the olefinic carbon signals and a reduced splitting of the allylic carbon signals. The shifts agree well with an earlier ab initio study. C‐H couplings are shown to be another probe for the charge delocalization in 2 .