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2004 | 2 | 4 | 563-572
Tytuł artykułu

HPLC monitored synthesis of R2NCH2 substituted benzene derivatives used as (C,N)-ligands for organometallic compounds

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
2-(Diethylaminomethyl)phenyl bromide and 1,3-bis(dimethylaminomethyl)-benzene, useful ligands for the synthesis of hypervalent organometallic compounds, were prepared and characterized by NMR (1H, 13C, 2D experiments) spectroscopy. Their synthesis was monitored by the HPLC method. The compounds were eluted on a Nucleosil 120 Si column (5 μm, 25×0.4 cm) with n-hexane at room temperature using a 1.0 ml/min flow-rate. The maximum values of absorbance for the studied compounds, excepting the diethylamine, were located in a narrow range around 212 nm, the wavelength used for their UV detection. The diethylamine was detected at 190 nm. The calibration curves are straight lines with correlation factors r>0.995. The HPLC data are in good agreement with those provided by NMR spectroscopy.
Wydawca

Czasopismo
Rocznik
Tom
2
Numer
4
Strony
563-572
Opis fizyczny
Daty
wydano
2004-12-01
online
2004-12-01
Twórcy
  • “Raluca Ripan” Institute for Research in Chemistry, 30 Fântânele Street, P.O. Box 702, RO-400294, Cluj-Napoca, Romania
  • “Raluca Ripan” Institute for Research in Chemistry, 30 Fântânele Street, P.O. Box 702, RO-400294, Cluj-Napoca, Romania, v.coman@icrr.itim-cj.ro
autor
  • Faculty of Chemistry and Chemical Engineering, “Babeş-Bolyai” University, 11 Arany Janos Street, RO-400028, Cluj-Napoca, Romania
  • Faculty of Chemistry and Chemical Engineering, “Babeş-Bolyai” University, 11 Arany Janos Street, RO-400028, Cluj-Napoca, Romania
Bibliografia
  • [1] C.J. Carmalt and A.H. Cowley: “Main group chemistry with arms”, Main Group Chem. News, Vol. 4, (1996), pp. 4–10 and references cited therein.
  • [2] R. Varga, M. Schuermann and C. Silvestru: “Hypervalent organotin(IV) derivatives containing [2-(Me2NCH2)C 6H4]Sn moieties. Competition between nitrogen and chalcogen atoms for coordination to the metal center”, J. Organomet. Chem., Vol. 623, (2001), pp. 161–167. http://dx.doi.org/10.1016/S0022-328X(00)00871-8[Crossref]
  • [3] J.E. Drake, M.B. Hursthouse, M. Kulcsar, M.E. Light and A. Silvestru: “Hypervalent tellurium compounds containing N→Te intramolecular interactions. Crystal and molecular structure of [2-(Me2NCH2)C 6H4]TeS(S)PR2 (R=Me, Ph, OPri ) and [2-(Me2NCH2)C 6H4]Te−S−PPh2=N−PPh2=S”, J. Organomet. Chem., Vol. 623, (2001), pp. 153–160. http://dx.doi.org/10.1016/S0022-328X(00)00739-7[Crossref]
  • [4] C. Deleanu, J.E. Drake, M.B. Hursthouse, M. Kulcsar, M.E. Light and A. Silvestru: “Hypervalent selenium compounds containing N→Se intramolecular interactions: synthesis, characterization and X-ray structures of [2-(Me2NCH2)C 6H4]SeS(S) PR2 (R=Ph, Oi Pr)”, Appl. Organomet. Chem., Vol. 16, (2002), pp. 727–731. http://dx.doi.org/10.1002/aoc.379[Crossref]
  • [5] L.M. Opris, A. Silvestru, C. Silvestru, H.J. Breunig and E. Lork: “Solid state structure and solution behaviour of hypervalent organoantimony halides containing 2-(Me2NCH2)C 6H4- moieties”, Dalton Trans., (2003), pp. 4367–4374.
  • [6] L. Balazs, H.J. Breunig, E. Lork and C. Silvestru: “Low-valent organobismuth compounds with intramolecular coordination: cyclo-R3Bi3, cyclo-R4Bi4, RBi[W(CO)5]2, and R4Bi2 [R=2-(Me2NCH2)C 6H4]”, Eur. J. Inorg. Chem., (2003), pp. 1361–1365.
  • [7] L. Balazs, O. Stanga, H.J. Breunig and C. Silvestru: “Hypervalent 5- Bi-12 derivatives containing dichalcogenoimidodiphosphinato ligands. Crystal structure and solution behaviour of [2-(Me2NCH2)C 6H4]BiCl[(XPR2)(YPR′2)N] (X, Y=O, S, Se; R, R′=Me, Ph)”,Dalton Trans., (2003), pp. 2237–2242.
  • [8] V. Meyer: Practical High-Performance Liquid Chromatography, 3rd Ed., John Wiley & Sons Ltd., Chichester, 1998.
  • [9] V. Antonucci, J. Kelly, L. Wright, N. Yasuda, M. Jensen, C. Yang and R.J. Reamer: “Development of chromatographic methods to monitor the synthesis of (tributylstannyl)methanol through unstable lithiated intermediates”, J. Chromatogr. A, Vol. 840, (1999), pp. 215–223. http://dx.doi.org/10.1016/S0021-9673(99)00240-X[Crossref]
  • [10] H. Shaw, H.D. Perlmutter and C. Gu: “Free-radical bromination of selected organic compounds in water”, J. Org. Chem., Vol. 62, (1997), pp. 236–237. http://dx.doi.org/10.1021/jo950371b[Crossref]
  • [11] I.C.M. Wehman-Ooyevaar, I.F. Luitwieler, K. Vatter, D.M. Grove, W.J.J. Smeets, E. Horn, A.L. Spek and G. van Koten: “Intramolecular C−H activation and oxidative addition reactions of iridium complexes containing arylamines with bulky substituents on nitrogen; X-ray structures of [IrI (C 6H4CH2NEt2-2- C,N)(cod)] and [IrIII (C 6H4CH2NEt (CHMe)-2- C,N,C″)I(cod)] (cod=cycloocta-1,5-diene”, Inorg. Chim. Acta, Vol. 252, (1996), pp. 55–69. http://dx.doi.org/10.1016/S0020-1693(96)05298-X[Crossref]
  • [12] Y. Yamamoto, X. Chen, S. Kojima, K. Ohdoi, M. Kitano, Y. Doi and K. Akiba: “Experimental investigation on edge inversion at trivalent bismuth and antimony: great acceleration by intra- and intermolecular nucleophilic coordination”, J. Am. Chem. Soc., Vol. 117, (1995), pp. 3922–3932. http://dx.doi.org/10.1021/ja00119a005[Crossref]
  • [13] K.R. Wursthorn, H.G. Kuivila and G.F. Smith: “Nucleophilic aromatic substitution by organostannylsodiums. A second-order reaction displaying a solvent cage effect”, J. Am. Chem. Soc., Vol. 100, (1978), pp. 2779–2789. http://dx.doi.org/10.1021/ja00477a034[Crossref]
  • [14] P.R. Markies, R.M. Altink, A. Villena, O.S. Akkerman, F. Bickelhaupt, W.J.J. Smeets and A.L. Spek: “Intramolecularly coordinated arylmagnesium compounds: effects on the Schlenk equilibrium”, J. Organomet. Chem., Vol. 402, (1991), pp. 289–312. http://dx.doi.org/10.1016/0022-328X(91)86244-K[Crossref]
  • [15] T. Shimizu, M. Enomoto, H. Taka and N. Kamigata: “Optical resolution and configurational stability of selenoxides stabilized by intramolecular coordination”, J. Org. Chem., Vol. 64, (1999), pp. 8242–8247. http://dx.doi.org/10.1021/jo990993n[Crossref]
  • [16] A.G. Avent, P.B. Hitchcock, G.J. Leight and M. Togrou: “The lithiation of arylamines and the preparation of cyclopentadienyltitanium(IV) arylaminate complexes”, J. Organomet. Chem., Vol. 669, (2003), pp. 87–100. http://dx.doi.org/10.1016/S0022-328X(02)02222-2[Crossref]
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02482721
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