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Synthesis and reactivity of chiral tellurium azomethines: Pseudopolymorphism of [o-((((1S,2R)-2-hydroxy-2-phenyl-1-methylethyl)amino)methinyl)phenyl] tellurium(IV) bromide

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Title Synthesis and reactivity of chiral tellurium azomethines: Pseudopolymorphism of [o-((((1S,2R)-2-hydroxy-2-phenyl-1-methylethyl)amino)methinyl)phenyl] tellurium(IV) bromide
 
Creator MENON, SC
SINGH, HB
PATEL, RP
DAS, K
BUTCHER, RJ
 
Subject sigmatropic rearrangement
molecular-structure
crystal-structure
first example
coordination
ligands
trichloride
ditelluride
chemistry
oxidation
 
Description A range of novel chiral tellurium compounds having an azomethine functional group in the position ortho to tellurium has been synthesized by the reaction of the tellurium-containing aldehydes bis(o-formylphenyl) telluride (1) and o-(butyltelluro)benzaldehyde (4) with chiral amines (R)-(+)-(1-pheylethylamine) and (1R,2S)-(-)-norephedrine, respectively. The precursor aldehydes were prepared by using a reported procedure with slight but advantageous modifications. During the preparation of o-(butyltelluro)benzaldehyde, interesting side products, namely bis(o-formylphenyl) ditelluride ethylene acetal 5, bis(o-formylphenyl) tritelluride (6), and bis(o-formylphenyl) ditelluride (7) were isolated in moderate yields. The ditelluride 7 has been characterized by single-crystal X-ray diffraction studies. The liquid Schiff bases 10 and 11 were further characterized by derivatizing with liquid bromine. The title compound was obtained in excellent yield by reacting the Schiff base 11 with elemental bromine. Detailed NMR studies indicated the presence of a rigid environment for the hydroxyl group. Single-crystal X-ray determinations of the crystals obtained from the different batches indicated. the presence of the two pseudopolymorphic forms 13a and 13b, respectively. In the case of 13a there is one molecule of CH3CN as solvent of crystallization, whereas in 13b half a molecule of CH3CN per molecule of the title compound lies along the 2-fold axis. In 13a the hydroxyl hydrogen is hydrogen-bonded to the nitrogen of the solvent molecule, whereas in 13b it is hydrogen-bonded to the bromine of the neighboring molecule.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T23:41:17Z
2011-12-26T12:49:07Z
2011-12-27T05:34:51Z
2011-07-14T23:41:17Z
2011-12-26T12:49:07Z
2011-12-27T05:34:51Z
1997
 
Type Article
 
Identifier ORGANOMETALLICS, 16(4), 563-571
0276-7333
http://dx.doi.org/10.1021/om9604280
http://dspace.library.iitb.ac.in/xmlui/handle/10054/4097
http://hdl.handle.net/10054/4097
 
Language en