Ph. D. THESIS 2009
Ph. D. THESIS 2009
Ph. D. THESIS 2009
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Figu re 4 . Th e 13<br />
C-NMR APT (CDCl , 1 2 5 MHz) sp e ct r u m o f<br />
3<br />
co m p o u n d 2<br />
The bridgehead tertiary carbon atoms at 1-C/5-C are located in the 13 C-<br />
NMR APT spectrum at resonance δ= 32.64 ppm.<br />
In conclusion, the missing of a deshielded signal pertaining to the enol<br />
protons in 1 H NMR spectrum, as well as the presence of a highly deshielded<br />
signal at δ= 208.59 ppm in the 13 C NMR spectrum, characteristic to the<br />
quaternary carbonyl atom, suggests the preference for the ketone form in the<br />
case of compound 2. Also, the conversion of 1 to 2 and the common elements<br />
of the NMR spectra of these compound are stated to confirm the presence of<br />
the bicyclo[3.3.1]nonane skeleton into the structure of compound 2.<br />
1 .3 .2 . FT-IR in ve stigatio n o f tetram eth y l 3 , 7 -<br />
d ih y d ro xy bicy clo [3 .3 .1 ] n o n a -2 , 6 -d ien e -2 , 4 , 6 , 8 -<br />
tetracarbo xy late<br />
One of the most suitable tools to investigate the nature of the hydrogen bonds<br />
in the bicyclic tetraester 1 is the FT-IR spectroscopy in solution. The<br />
experimental study consisted of the IR spectra registration in solution for<br />
compound 1 [10] in order to investigate the behavior of substance in terms of<br />
maintaining the hydrogen bonds and the way in which specific peaks of the<br />
form enol changes with solvent polarity.<br />
Theoretical spectra of conf_A and conf_B have been modeled to be compared<br />
with experimental spectrum in order to identify which is the preferred<br />
12