PREPARATIVE SEPARATION OF <i>CIS</i>- AND <i>TRANS</i>-1,2-DIAMINOCYCLOHEXANE MIXTURE BY MEANS OF THE SELECTIVE NICKEL(II) COMPLEX FORMATION

Saito, Reiko; Kidani, Yoshinori

doi:10.1246/cl.1976.123

Cited by 37 publications

(17 citation statements)

References 2 publications

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“…isomers as described in the literature [4]. Elemental analyses were carried out by the Analytical Section of the Institute for Applied Chemistry, T.N.O., Utrecht (The Netherlands).…”

Section: [(R)(s)] and Truns-[(r)(r)(s)(s)]mentioning

confidence: 99%

Syntheses and characterization of neutral complexes of Zn(II) with mono- and dianionic pyrrole-2-imine ligands [(pyrrole-2-CHN)nR]n− (n = 1, 2)

Stein

Koten

Passenier

et al. 1984

Inorganica Chimica Acta

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“…isomers as described in the literature [4]. Elemental analyses were carried out by the Analytical Section of the Institute for Applied Chemistry, T.N.O., Utrecht (The Netherlands).…”

Section: [(R)(s)] and Truns-[(r)(r)(s)(s)]mentioning

confidence: 99%

Syntheses and characterization of neutral complexes of Zn(II) with mono- and dianionic pyrrole-2-imine ligands [(pyrrole-2-CHN)nR]n− (n = 1, 2)

Stein

Koten

Passenier

et al. 1984

Inorganica Chimica Acta

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“…The Ni (II) [68] were prepared by modified literature procedures. FTIR spectra were obtained as KBr pellets on a Perkin-Elmer 100FTIR spectrometer (Perkin-Elmer, Seer Green, UK).…”

Section: Generalmentioning

confidence: 99%

Oxidoborates Templated by Cationic Nickel(II) Complexes and Self-Assembled from B(OH)3

2021

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Several oxidoborates, self-assembled from B(OH)3 and templated by cationic Ni(II) coordination compounds, were synthesized by crystallization from aqueous solution. These include the ionic compounds trans-[Ni(NH3)4(H2O)2][B4O5(OH)4].H2O (1), s-[Ni(dien)2][B5O6(OH)4]2 (dien = N-(2-aminoethyl)-1,2-ethanediamine (2), trans-[Ni(dmen)2(H2O)2] [B5O6(OH)4]2.2H2O (dmen = N,N-dimethyl-1,2-diaminoethane) (3), [Ni(HEen)2][B5O6(OH)4]2 (HEen = N-(2-hydroxyethyl)-1,2-diaminoethane) (4), [Ni(AEN)][B5O6(OH)4].H2O (AEN = 1-(3-azapropyl) -2,4-dimethyl-1,5,8-triazaocta-2,4-dienato(1-)) (5), trans-[Ni(dach)2(H2O)2][Ni(dach)2] [B7O9(OH)5]2.4H2O (dach = 1,2-diaminocyclohexane) (6), and the neutral species trans-[Ni(en)(H2O)2{B6O7(OH)6}].H2O (7) (en = 1,2-diaminoethane), and [Ni(dmen)(H2O){B6O7(OH)6}].5H2O (8). Compounds 1–8 were characterized by single-crystal XRD studies and by IR spectroscopy and 2, 4–7 were also characterized by thermal (TGA/DSC) methods and powder XDR studies. The solid-state structures of all compounds show extensive stabilizing H-bond interactions, important for their formation, and also display a range of gross structural features: 1 has an insular tetraborate(2-) anion, 2–5 have insular pentaborate(1-) anions, 6 has an insular heptaborate(2-) anion (‘O+’ isomer), whilst 7 and 8 have hexaborate(2-) anions directly coordinated to their Ni(II) centers, as bidentate or tridentate ligands, respectively. The Ni(II) centers are either octahedral (1–4, 7, 8) or square-planar (5), and compound 6 has both octahedral and square-planar metal geometries present within the structure as a double salt. Magnetic susceptibility measurements were undertaken on all compounds.

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“…n$ = 1,5078. 1R (CHCI,): 2950% 2895m, 1675s, 1580m,1490w, 1450m, 1400m, 1310m, 1245s, 1 loom, 1070m, 975w, 900s (54),59 (4% 51 (1% 50 (1% 45 (12), 43 (13), 28 (5).…”

Section: -Methoxy-nnnn'-tetramethyibenzolmethandiumin (Lc)mentioning

confidence: 99%

“…H m zu CH,); 2,36 (s, CH,); 0,25 (s,(CH,), Si).MS: 193 (20), 192 (55), 191 (38, M'). 190 (30), 177 (14), 176 (87), 163 (ll), 150(12), 149 (79), 133(12), 119(41), 118(69), 105(14),91 (94),89(35),77(12),76(10),75(78),73(100),65(49), 59 N-(4-Methoxybenzyliden) (rrimethylsilyl)umin (3c). Nach AAV I wurden 18,2 ml (0,15 mol) Anisaldehyd umgesetzt.…”

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Anwendungsbreite der reduktiven Kupplung aromatischer Aldimin‐Derivate mit niedervalenten Titan‐Reagenzien zu 1,2‐Diarylethylendiaminen

Betschart

Schmidt

Seebàch

1988

Helvetica Chimica Acta

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Besides the adducts from lithium amides to aromatic aldehydes, iminium salts, aminals, and N-silylimines of aromatic aldehydes are coupled by the black suspension obtained from TiCI, and Mg turnings in tetrahydrofuran (THF). The 1,2-diarylethylenediamines with tertiary and primary amino groups thus obtained are formed with no or only moderate diastereoselectivity (products 4a-d (Scheme 2) and 5a-e (Scheme 3), respectively); the amine component may contain a strained ring or additional heteroatoms as in azetidin, bis(2-methoxyethyl)amine, piperazine, morpholine, and thiomorpholine (products 6a-e; Table .I). By an in-situ procedure, ethylenediamines and propane-l,3-diamines with two secondary amino groups are cyclized with aromatic aldehydes to give exclusively trans-diaryl-substituted piperazine and perhydro-1 ,4-diazepine derivatives (products 7a-f; Table 2). Enantiomerically pure monocyclic trans,cis-5-alkyl-2,3-diaryl-piperazines and diazabicyclo[4.3.0]nonanes and -[4.4.0]decanes are obtained by employing suitable diamines prepared from the amino acids (S)-alanine, (S)-phenylalanine, (S)-proline, and from (S,S)-or (R,R)-cyclohexane-l,2-diamine, respectively (products 1 la-i, 7e; Table 4 ) . The configurations of all products are derived from the high-field NMR spectra, some of which are discussed in detail (Figs. I and 2, Tables 3 and 5 ) ; all new compounds are fully characterized by their physical data.Depending upon the structure of the components employed, the yields of purified products range from as low as 7 % to essentially quantitative. ' ) 4, Je ein Beispiel (p-Toluylaldehyd-Derivate) wurde schon fruher beschrieben [2]. Bei Zugabe von 1 Aquiv. TiCI, zur Losung des Aminals in Hexan erhielt man eine hellgelbe Suspension, die ein Iminium-Salz enthalten konnte. Die anschliessende Kupplungsreaktion rnit dem niedervalenten Ti-Reagens lieferte die Diamine jedoch nicht in besserer Ausbeute als die direkte Umsetzung des Aminals. Nach [3] lisst sich das Iminium-chlorid 2b auch durch mehrstundiges Ruhren rnit Mg in THF bei 40" kuppeln. Die Autoren beschreiben als Produkt nur das meso-Diamin (Schmp. und 'H-NMR-Spektrum), ohne das zweite Diastereoisomere zu erwahnen. Eine Wiederholung dieses Experiments lieferte jedoch ebenfalls ein nahezu (1 : 1)-Gemisch der Diastereoisomeren. *) HELVETICA CHIMICA ACTA -Vol. 71 (1988) Schema 2 200 1 l a X = H b X=CH, c X=CH,O d X=Br meso/rac ca. 1 : 1 92% 4% x=n 92% 100% b X=CH, 100% 95% c X=CH,O 93% 100% d X=Br 91% 2a X = H b X=CH, c X=CH,O d X=Br vor kurzem eine praktikable Methode zur Herstellung der Diamine mit primaren Amino-Gruppen bekannt geworden: NbC1, als Kupplungsreagens fur N-Silylimine 3 [4]. Es zeigt sich, dass diese leicht zuganglichen Silyl-Derivate auch mit dem niedervalenten Ti-Reagens zu Diaminen 5 gekuppelt werden konnen (Schema 3 ) . Neben den bevorzugt in der ruc-Form auftretenden Produkten 5 (ruclmeso bis 6 : l ) bilden sich bis zu 20% als einfache Reduktionsprodukte die Benzylamine (vgl. Exper. Teil). 6,6,9-Trimethyl-7.8-diphenyl-9-azu-6-uzoniaspiro[3.6]dec...

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PREPARATIVE SEPARATION OF CIS- AND TRANS-1,2-DIAMINOCYCLOHEXANE MIXTURE BY MEANS OF THE SELECTIVE NICKEL(II) COMPLEX FORMATION

Cited by 37 publications

References 2 publications

Syntheses and characterization of neutral complexes of Zn(II) with mono- and dianionic pyrrole-2-imine ligands [(pyrrole-2-CHN)nR]n− (n = 1, 2)

Syntheses and characterization of neutral complexes of Zn(II) with mono- and dianionic pyrrole-2-imine ligands [(pyrrole-2-CHN)nR]n− (n = 1, 2)

Oxidoborates Templated by Cationic Nickel(II) Complexes and Self-Assembled from B(OH)3

Anwendungsbreite der reduktiven Kupplung aromatischer Aldimin‐Derivate mit niedervalenten Titan‐Reagenzien zu 1,2‐Diarylethylendiaminen

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