N. Psychogios, J.-B. Regnouf-de-Vains / Tetrahedron Letters 43 (2002) 7691–7693
7693
−
5
−3
Figure 2. UV–vis titration of 6 by Cu(MeCN) PF . 6 2.0×10 M in H O; (f) 6+1 equiv. of Cu(I); (g) (f)+1 equiv. of BSA 10
4
6
2
−
3
M in H O (40 mL); (h) (f)+10 equiv. of BSA 10 M in H O (400 mL).
2
2
trometry showed, with a bad resolution, the presence of
D.; Pagoria, P. F. J. Org. Chem. 1985, 50, 5795; (c)
Gutsche, C. D.; Alam, I. Tetrahedron 1988, 4689.
2. Almi, M.; Arduini, A.; Casnati, A.; Pochini, A.; Ungaro,
R. Tetrahedron 1989, 45, 2177.
+
−
the monocharged species [6-Na ] ; the better informa-
tion obtained with di- and tricharged species (Fig. 1),
confirmed the formation of 6.
3. Gutsche, C. D.; Nam, K. C. J. Am. Chem. Soc. 1988,
6
,7
As in the previous reports, the complexing ability of
towards Cu(I) salts was observed in water by UV–vis
spectroscopy. The addition of Cu(MeCN) PF in an
110, 6153.
6
4. (a) Shinkai, S.; Mori, S.; Tsukabi, T.; Sone, T.; Manabe,
O. Tetrahedron Lett. 1984, 25, 5315; (b) Shinkai, S.;
Araki, K.; Tsukabi, T.; Arimura, T.; Manabe, O. J.
Chem. Soc., Perkin Trans. 1 1987, 2297.
4
6
aqueous solution of the ligand resulted in the formation
of a 1:1 complex characterised by the specific metal-to-
ligand charge transfer (MLCT) band at ca. 455 nm
encountered in tetrahedral copper(I)/heterocycle com-
plexes (Fig. 2).
5. For example: (a) Regnouf-de-Vains, J.-B.; Lamartine, R.;
Fenet, B. Helv. Chim. Acta 1998, 81, 661; (b) Pellet-Ros-
taing, S.; Regnouf-de-Vains, J.-B.; Lamartine, R.; Fenet,
B. Inorg. Chem. Commun. 1999, 2, 4; (c) Molard, Y.;
Bureau, C.; Parrot-Lopez, H.; Lamartine, R.; Regnouf-
de-Vains, J.-B. Tetrahedron Lett. 1999, 40, 6383; (d)
Dalbavie, J.-O.; Regnouf-de-Vains, J.-B.; Lamartine, R.;
Lecocq, S.; Perrin, M. Eur. J. Inorg. Chem. 2000, 4, 683;
(e) Dalbavie, J.-O.; Regnouf-de-Vains, J.-B.; Lamartine,
R.; Lecocq, S.; Perrin, M.; Fenet, B. Eur. J. Inorg. Chem.
2002, 4, 901.
A preliminary evaluation of the behaviour of this com-
plex in biological media was performed by addition of
BSA in the UV titration medium. The MLCT band
remained unchanged in these conditions, suggesting, as
6,7
for the two previous ligands, an interesting role of
cation carrier for biological applications. This point is
under current investigation.
6. Psychogios, N.; Regnouf-de-Vains, J.-B. Tetrahedron
Lett. 2002, 43, 77.
Acknowledgements
7. Psychogios, N.; Regnouf-de-Vains, J.-B. Tetrahedron
Lett. 2001, 42, 2799.
8. Almi, M.; Arduini, A.; Casnati, A.; Pochini, A.; Ungaro,
We are grateful to the MRES and to the CNRS for
financial support, and to SAFAS (Monaco) for UV
spectroscopy. The authors thank Mr. J.-M. Ziegler for
mass measurements and Mrs. N. Marshall for correct-
ing the manuscript.
R. Tetrahedron 1989, 45, 2177.
9. Wieser-Jeunesse, C.; Matt, D.; Yaftian, M. R.; Burgard,
M.; Harrowfield, J. M. C.R. Acad. Sci., Ser. IIc: Chim.
1998, 1, 479.
10. Solovyov, A.; Cherenok, S.; Tsymbal, I.; Failla, S.; Con-
siglio, G. A.; Finocchiaro, P.; Kalchenko, V. Heteroatom
Chem. 2001, 12, 58.
References
11. Huang, Z.-T.; Wang, G.-Q.; Yang, L.-M.; Lou, Y.-X.
Synth. Commun. 1995, 25, 1109.
1
. (a) Arduini, A.; Pochini, A.; Reverberi, S.; Ungaro, R. J.
Chem. Soc., Chem. Commun. 1984, 981; (b) Gutsche, C.
12. Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.;
Sanchez, C. J. Org. Chem. 1991, 56, 3372.