Ph.D. THESIS ABSTRACT SYNTHESIS, STEREOCHEMISTRY AND ...

Radu Gropeanu – PhD Thesis Abstract
to the two magnetic equivalent phenothiazine units, and the vinylic protons as a singlet (δ = 6.55
ppm) (Figure 3).
7.5
7.0
6.5
Figure 3. The 1 H-NMR spectrum of 31 (CDCl3, 300 MHz, r.t.)
6.0
5.5
5.0
4.5
The mass spectrum is in accordance with the assigned structure.
The X-rays analysis performed on monocrystal showed us that the vinylene bridge
presents the cis configuration, and that the two phenothiazine units lie in an anti orientation.
These phenothiazine units are a little beat twisted from a superposed arrangement, which is
preferred by the bis(phenothiazinyl)ferrocene derivatives (Figure 4). This fact suggests an
electronic communication between the two phenothiazines through the vinylene bridge. The
other atropisomer (with a syn orientation of the phenothiazinic units) could not been detected by
means of NMR spectrometry. Also, whilst there are described ferrocene macrocycles formed by
McMurry reductive coupling with the resulted vinylene bridge having both cis and trans
configurations, the trans isomer of 31 was not isolated.
a b
Figure 4. The ORTEP drawing of 31: a) view along a perpendicular axis to the cyclopentadienyl rings; b)
view along a parallel axis with the cyclopentadienyl rings
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5
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