Record Details

Synthesis and structural characterization of pincer type bicyclic diacyloxy- and diazaselenuranes

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Synthesis and structural characterization of pincer type bicyclic diacyloxy- and diazaselenuranes
 
Creator SELVAKUMAR, K
SINGH, HB
GOEL, N
SINGH, UP
BUTCHER, RJ
 
Subject 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
 
Description 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.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2012-06-26T09:30:19Z
2012-06-26T09:30:19Z
2011
 
Type Article
 
Identifier DALTON TRANSACTIONS,40(38)9858-9867
1477-9226
http://dx.doi.org/10.1039/c1dt10862j
http://dspace.library.iitb.ac.in/jspui/handle/100/14291
 
Language English