The Reactivity of Diorganotellurium Oxides Towards Phenol and o-Nitrophenol. Hypervalent and Secondary Bonding of Four Different Product Classes

Jens Beckmann; Jens Bolsinger; Andrew Duthie

doi:10.1071/CH07329

RESEARCH ARTICLE

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The Reactivity of Diorganotellurium Oxides Towards Phenol and o-Nitrophenol. Hypervalent and Secondary Bonding of Four Different Product Classes

Jens Beckmann ^A ^C , Jens Bolsinger ^A and Andrew Duthie ^B

+ Author Affiliations

- Author Affiliations

^A Institut für Chemie und Biochemie, Freie Universität Berlin, Fabeckstrasse 34/36, 14195, Berlin, Germany.

^B School of Life and Environmental Sciences, Waurn Ponds, Vic. 3216, Australia.

^C Corresponding author. Email: Beckmann@chemie.fu-berlin.de

Australian Journal of Chemistry 61(3) 172-182 https://doi.org/10.1071/CH07329
Submitted: 16 September 2007 Accepted: 8 February 2008 Published: 26 March 2008

Abstract

The reaction of the diorganotellurium oxides R₂TeO (R = Ph, p-MeOC₆H₄, p-Me₂NC₆H₄) with phenol and o-nitrophenol produces diorganotellurium hydroxy phenolates, R₂Te(OH)OPh (1, R = Ph; 2, R = p-MeOC₆H₄; 3, R = p-Me₂NC₆H₄), diorganotellurium bis(phenolates) R₂Te(OPh)₂ (4, R = Ph; 5, R = p-MeOC₆H₄; 6, R = p-Me₂NC₆H₄), tetraorganoditelluroxane bis(o-nitrophenolates), (R′O)R₂TeOTeR₂(OR′) (7, R = p-MeOC₆H₄; 8, R = p-Me₂NC₆H₄; R′ = o-NO₂C₆H₄), and a hexaphenyltritelluroxane bis(o-nitrophenolate) (R′O)Ph₂TeOTePh₂OTePh₂(OR′) (9, R′ = o-NO₂C₆H₄), respectively. The redistribution reactions of R₂Te(OPh)₂ (4, R = Ph; 5, R = p-MeOC₆H₄; 6, R = p-Me₂NC₆H₄) with the corresponding diorganotellurium oxides R₂TeO and diorganotellurium dichlorides R₂TeCl₂ (R = Ph, p-MeOC₆H₄, p-Me₂NC₆H₄) give rise to the formation of moisture sensitive tetraorganoditelluroxane bis(phenolates) (PhO)R₂TeOTeR₂(OPh) (10, R = Ph; 11, R = p-MeOC₆H₄; 12, R = p-Me₂NC₆H₄) and diorganotellurium chloro phenolates, R₂Te(Cl)OPh (13, R = Ph; 14, R = p-MeOC₆H₄; 15, R = p-Me₂NC₆H₄), respectively. The reaction of the diorganotellurium oxides R₂TeO with the corresponding diorganotellurium dichlorides R₂TeCl₂ (R = Ph, p-MeOC₆H₄, p-Me₂NC₆H₄) affords tetraorganoditelluroxane dichlorides ClR₂TeOTeR₂Cl (16, R = Ph; 17, R = p-MeOC₆H₄; 18, R = p-Me₂NC₆H₄) as air-stable solid materials. The reactivity of 1–18 can be rationalized by the kinetic lability of the Te–O and Te–Cl bonds. Compounds 1–18 have been characterized by solution and solid-state ¹²⁵Te NMR spectroscopy and 2, 4, 6, 7, 9, 17, and 18 have also been analyzed by X-ray crystallography.

Acknowledgement

Mrs. Irene Brüdgam (Freie Universität Berlin) is thanked for the X-ray data collection. The Deutsche Forschungsgemeinschaft (DFG) is gratefully acknowledged for financial support.

References

The Reactivity of Diorganotellurium Oxides Towards Phenol and o-Nitrophenol. Hypervalent and Secondary Bonding of Four Different Product Classes

Abstract

Acknowledgement

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