Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/xmlui/handle/100/14266
Title: Methyl Ester Function: An Intramolecular Electrophilic Trap for the Isolation of Aryltellurenyl Hydroxide and Diorganotellurium Dihydroxide
Authors: SELVAKUMAR, K
SINGH, HB
GOEL, N
SINGH, UP
Keywords: Diaryl Tellurides
Photosensitized Oxygenation
Telluroxide Elimination
Oxidizing Properties
Staudinger Ligation
Molecular-Structure
Allylic Alcohols
Peroxidase
Derivatives
Selenium
Issue Date: 2011
Publisher: AMER CHEMICAL SOC
Citation: ORGANOMETALLICS,30(14)3892-3896
Abstract: The formation of an aryltellurenyl hydroxide analogue proposed in the telluroxide elimination reaction has been studied. The reaction of the monotelluride dimethyl 5-tert-butyl-2-(butyltellanyl)isophthalate (6) with H(2)O(2) afforded the corresponding aryldiacyloxy-n-butyltellurane (8). The reaction of 6 with oxygen in the presence of moisture resulted in the formation of 8 as the major product along with traces of dimethyl 5-tert-butyl-2-(butyltellurinyl)isophthalate (7) and methyl 5-tert-butyl-3-oxo-3H-benzo[c][1,2]oxa tellurole-7-carboxylate (9). The telluroxide intermediate 7 readily undergoes a facile elimination reaction to give the elusive aryltellurenyl hydroxide, which is immediately trapped by the adjacent methyl ester functionality to give the cyclic tellurenate ester 9. Similarly, the hydrolysis of 7 with H(2)O affords the corresponding dihydroxytellurane 10, which is immediately converted to tellurane 8. Both compounds 8 and 9 have been characterized by single-crystal X-ray crystallographic studies.
URI: http://dx.doi.org/10.1021/om2001553
http://dspace.library.iitb.ac.in/jspui/handle/100/14266
ISSN: 0276-7333
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