NDLI: Controlled hydrolysis of aryltellurium trichlorides using 2-pyrrolidinones: isolation and structural characterization of monomeric aryltellurium(IV) monohydroxides

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Controlled hydrolysis of aryltellurium trichlorides using 2-pyrrolidinones: isolation and structural characterization of monomeric aryltellurium(IV) monohydroxides

Content Provider	Royal Society of Chemistry (RSC)
Author	Butcher, R. J. Misra, Shafalika Srivastava, Ramesh C. Duthie, Andrew Chauhan, Ashok K. S.
Copyright Year	2011
Abstract	The 2-pyrrolidinone (Pyrr)-assisted hydrolysis of aryltellurium trichlorides, provided their first-step hydrolysis products as 1 : 1 molecular adducts, ArTeCl2OH.Pyrr (Ar = 1-C10H7, Npl, 1; 2,4,6-Me3C6H2, Mes, 2). The hydroxo ligand occupies an equatorial position in the ψ-trigonal bipyramidal geometry around Te(IV) and is involved in a strong H-bonding interaction with the amido O of the base. As NplTeBr3 did not react with 2-pyrrolidinone under similar conditions, the bromo analogue of 1, NplTeBr2OH.Pyrr (3), was prepared by a metathetical reaction with NaBr. Both 1 and 2 undergo electrophilic substitution with acetone and pinacolone to afford Ar(RCOCH2)TeCl2 (R = Me, t-Bu), but do not react with iodoacetic acid, suggesting that the hydroxo ligand acts as a nucleophile rather than a base. The Te–OH bond in 1 is also cleaved by CH3COCl to give the parent trihalide NplTeCl3, while reaction with BrCH2COBr results in NplTeBr3 (4) as the ultimate tellurium containing product. The reaction of NplTeCl3 with N-Methyl protected 2-pyrrolidinone (PyrrMe), under similar conditions, gave an ionic complex [(PyrrMe)2H] [NplTeCl4] (5), but did not react with N-acyl protected 2-pyrrolidinone, PyrrCOCH2Br. However, the latter added oxidatively to elemental tellurium to give (PyrrCOCH2)2TeBr2 (6). In the crystal lattice of 5, discreet five-coordinate square pyramidal CTeX4 units are present, while in the case of 4 the same units are realized via intermolecular Te⋯Br interactions in a one-dimensional supramolecular architecture. N-(2-pyrrolidinone)amidomethyl ligands in 6 adopt a rare, if not the first, 1,6-(C,O) mode of chelation in preference to 1,4-(C,O) mode often observed in similar Te(IV) compounds.
Starting Page	808
Ending Page	816
Page Count	9
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	1
Issue Number	5
Journal	RSC Advances
DOI	10.1039/c1ra00409c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Hydrolysis Pinacolone Electrophilic aromatic substitution Ligand Covalent bond Npl Tellurium Molecular geometry Acetone Nucleophile Crystal structure
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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