Molbank 2006, M456 |
Synthesis
of N,N'-bis (a-methylsalicylidene)
4,4'-diaminodiphenylmethane as a novel complexing
agent
A. A. Jarrahpour*, S. Rezaei
Department of Chemistry,
Phone: +98 711 2284822, Fax: +98
711 2280926, e-mail: [email protected] and [email protected]
*Author to whom
correspondence should be addressed
Received:
Keywords: 2-Hydroxyacetophenone, 4,4'-diaminodiphenylmethane,
Schiff base
Schiff
base ligands are used in complexation
with metals such as V(II) for the enantioselective
oxidation of sulfides to chiral sulfoxides.An
increasing number of chiral sulfoxides
are becoming useful chiral auxiliaries in asymmetric
synthesis [1].Cameron and his co-workers have shown that Schiff base ligands are capable of stabilising
cationic methylaluminium centres
only when they possess an additional donor arm [2].Synthesis and spectroscopic
studies of the optically active copper(II), cobalt(II) and nickel(II) complexes
with Schiff bases have been studied by Szlyk
[3].Schiff base ligands have been used in several
catalytic asymmetric reactions [4]. Metal complex Schiff bases have also been
used in oxidation reactions [5].
3 2 1
2-Hydroxyacetophenone
1 (2.03g, 1.8 mL, 15.00 mmol) and 4,4'-diaminodiphenylmethan 2 (0.99 g, 5.00 mmol) were dissolved in
10 mL of warm ethanol. The reaction mixture was
refluxed for 14h.The solid product was filtered off and washed with ethanol.
The pure Schiff base 3 was
obtained as a yellow solid (yield 78%)
Melting
Point: 120¡ãC
IR (KBr, ¦Í, cm-1):
3244 (OH); 1647 (C=N).
1H-NMR (250 MHz, CDCl3): ¦Ä= 2.20 (6H, s, ArCH3);
3.87(2H, s, Ar-CH2); 6.61 (2H, d, Ar); 7.06-7.96 (5H, m, Ar); 14.86
(2H, s, OH).
13C-NMR (62.9 MHz, CDCl3): ¦Ä= 17.06; 40.88;
11.35; 11.24; 12.57; 128.89; 129.52; 129.76; 132.96; 137.67; 138.64; 162.07;
171.24.
MS (m/z): 434 (25%), 316 (37%), 198 (38%), 106
(87%), 77 (20%).
Acknowledgment
The authors thank the Shiraz University Research
Council for financial support (Grant No.84-GR-SC-23)
References:
1. Gama, A.;
Flores-L¨®pez, L. Z.; Aguirre,G.;
Hellberg, M. P. H.; Somanathan,
R. Arkivoc, 2003, 4-15.
2. Cameron, P. A.; Gibson, V. C.; Redshaw, C.; Segal, J. A.; Bruce, M. D.; White, A.; Williams, D. Chem. Commun., 1999, 1883¨C1884.
3. Szłyk, E.; Barwiołek,
M.; Kruszynski, R.; Bartczak,
T. Inorg. Chim. Acta, 2005,
358. 3642-3652.
4. Flores-lopez, L. Z.; Parra-Hake, M. P.; Somanathan, R.; Walsh, P. J.; Organometallics, 2000, 19, 2153-2160.
5. Kervinen, K.; Korpi, H.; Leskela, M.; Repo, T. J. Mol. Cat. 2003, 203, 9-19.
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