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136 D. Waumans et al. / Forensic Science International 143 (2004) 133–139<br />
preparations have been confiscated by Belgian Law<br />
Enforcement in 2001/2002 and have been transferred to<br />
our laboratory for investigation. Previous findings<br />
have meanwhile entered the published scientific literature<br />
(a)<br />
(b)<br />
(c)<br />
(d)<br />
1<br />
1<br />
1<br />
1<br />
m/z 268<br />
5.00 10.00 15.00 20.00 25.00 30.00<br />
min<br />
[10]. The screened preparations include two brownish<br />
powders (seized from different sources), a capsule containing<br />
a similarly appearing brownish powder, and a<br />
beige tablet bearing an ‘xTc’-logo. The latter has been<br />
20.00 21.00 22.00 23.00 24.00 25.00<br />
Fig. 2. Chromatograms: [a] performic acid oxidation in acetone [b] performic acid oxidation in DCM [c] peracetic acid oxidation in acetone<br />
[d] peracetic acid oxidation in DCM [e] extracted ion chromatogram (m/z 268) for retention time interval 20.00–25.00 from [a]. Mass<br />
spectrum: The diastereomers have identical mass spectra. The four theoretically possible diastereomers are shown. Reaction scheme: Anethole<br />
is epoxidized (A), after which the obtained <strong>anethole</strong> epoxide is converted to a stable carbocation (5) (B). Formation of <strong>neo</strong>lignan (1) follows<br />
from the interaction between (5) and <strong>anethole</strong> (C), which results in the formation of an unstable intermediary product prone to intramolecular<br />
rearrangements (E).<br />
O<br />
(e)<br />
O<br />
O<br />
(1)<br />
O<br />
O<br />
B<br />
E<br />
O<br />
OH<br />
O<br />
A<br />
+<br />
(5)<br />
+<br />
min<br />
OH<br />
O<br />
O<br />
C<br />
D<br />
OH<br />
O<br />
+<br />
O