1,1 `-2-Trisubstituted ferrocenyl dibismuthines containing N / O donor pendant arm
Por:
C, Claudia P. Villamizar, Anzaldo, Bertin, SHARMA, PANKAJ, Gonzalez, Rodary, Toscano, Alfredo, Pena, Maria A., Sharma, Manju, Gutierrez, Rene
Publicada:
21 dic 2020
Resumen:
New unsymmetrical chiral 1,1'-2-ferrocenyl dibismuthines [(C5H4)(BiPh2
)]Fe(2-{Me2NCH(R)C5H3)(BiPh2) containing 2-[(Me2NCH(R)] where R =
Me (1) or H (3) pendant arm on ferrocenyl ring were synthe-sized. An
unsymmetrical 1,1'-ferrocenyl-bismuthine (5) in a low yield and
1,1'-2-ferrocenyl chlorodibismuthine (11) as an impurity were also
isolated from the reaction mixture. Furthermore, Monoammonium salt
[CpFe{2-(Me3N +CH2)C5H3 (BiPh2)(2)][I-] (6) and
1,1,2-vinylferrocenyl dibismuthine derivative (7) were obtained by the
reaction of CH3I with (3) and (1) respectively. The nucleophilic
substitution reaction of (6) by o-hydroxyacetaphenone, salicylaldehyde,
and N-methyl piperazine in acetonitrile gave the new functionalized 1,1
`-2-substituted ferrocenyl dibismuthines
[(C5H4)(BiPh2)]Fe[{2-(RCH2)C5H3 BiPh2] where R = OC6H4-2-C(O)Me
(8), OC6H4-2-C(O)H (9) and N(CH2CH2)(2)NMe (10) respectively with
different N or O containing pendant arm. 1,2-disubstituted ferrocenyl
compounds presented in this work present planar chirality. These new
compounds were characterized by IR, H-1-NMR, C-13-NMR spectroscopy, and
High-Resolution Mass Spectrometry (HRMS). The X-ray structures of 1,1,'
2-trisubstituted ferrocenyl dibismuthines (10) and (11) were determined.
The molecular structure of (11) shows hypervalent BiN bonding in
the solid-state. The compound (11) has planar chirality, central
chirality, and Bi center-chirality with pseudo-trigonal bipyramidal
geometry (see-saw structure) around the chiral Bi center while the other
bismuth atom has distorted trigonal pyramidal geometry. The variable
temperature 1H-NMR spectra of compound (3) in -40 degrees C to 40
degrees C range in CDCl3 indicates a lack of BiN
coordination. (c) 2020 Elsevier B.V. All rights reserved.
Filiaciones:
C, Claudia P. Villamizar:
Univ Autonoma Mexico UNAM, Inst Quim, Cd Univ, Mexico City 04510, DF, Mexico
Anzaldo, Bertin:
Univ Autonoma Mexico UNAM, Inst Quim, Cd Univ, Mexico City 04510, DF, Mexico
BUAP, Fac Cs Quim, Lab Sintesis Complejos, Ciudad Univ,POB 72592, Puebla, Mexico
SHARMA, PANKAJ:
Univ Autonoma Mexico UNAM, Inst Quim, Cd Univ, Mexico City 04510, DF, Mexico
Gonzalez, Rodary:
Univ Autonoma Mexico UNAM, Inst Quim, Cd Univ, Mexico City 04510, DF, Mexico
Toscano, Alfredo:
Univ Autonoma Mexico UNAM, Inst Quim, Cd Univ, Mexico City 04510, DF, Mexico
Pena, Maria A.:
Univ Autonoma Mexico UNAM, Inst Quim, Cd Univ, Mexico City 04510, DF, Mexico
Sharma, Manju:
Inst Tecnol Milpa Alta, Dept Ingn, Mexico City 12300, DF, Mexico
Gutierrez, Rene:
BUAP, Fac Cs Quim, Lab Sintesis Complejos, Ciudad Univ,POB 72592, Puebla, Mexico
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