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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/14291

Title: Synthesis and structural characterization of pincer type bicyclic diacyloxy- and diazaselenuranes
Authors: SELVAKUMAR, K
SINGH, HB
GOEL, N
SINGH, UP
BUTCHER, RJ
Keywords: PEROXIDASE-LIKE ACTIVITY
ACTIVE ORGANOSELENIUM COMPOUND
CYCLIC SELENINATE ESTERS
GLUTATHIONE-PEROXIDASE
CRYSTAL-STRUCTURE
C-2-SYMMETRIC SPIROSELENURANE
NONBONDING INTERACTIONS
ABSOLUTE-CONFIGURATION
ENANTIOMERICALLY PURE
ANTIOXIDANT ACTIVITY
Issue Date: 2011
Publisher: ROYAL SOC CHEMISTRY
Citation: DALTON TRANSACTIONS,40(38)9858-9867
Abstract: Synthesis and structural characterization of a new class of pincer type bicyclic diacyloxy- and diazaselenuranes is reported. The reaction of dimethyl 2-bromo-5-tert-butylisophthalate (28) with sodium benzeneselenolate affords the corresponding monoselenide, dimethyl 5-tert-butyl-2-(phenylselanyl)isophthalate (29). Reduction of 29 with LiAlH(4) provides 5-tert-butyl-2-(phenylselanyl)-1,3-phenylene)dimethanol 31. Oxidation of 29 or its hydrolyzed derivative, 5-tert-butyl-2-(phenylselanyl) isophthalic acid (30), with H(2)O(2) results in the formation of bicyclic diacyloxyselenurane (25). The reaction of 30 with aniline using the DCC coupling reaction gives 5-tert-butyl-N(1),N(3)-diphenyl-2-(phenylselanyl)isophthalamide (38). Reaction of 38 with H(2)O(2) leads to the formation of the corresponding bicyclic diazaselenurane (27) via selenoxide intermediate 39. Compounds 25, 27, 29 and 31 were characterized by single crystal X-ray crystallography. The structural aspects of the pincer type bicyclic chalcogenuranes are investigated using experimental and computational studies and compared with the related systems.
URI: http://dx.doi.org/10.1039/c1dt10862j
http://dspace.library.iitb.ac.in/jspui/handle/100/14291
ISSN: 1477-9226
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