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Please use this identifier to cite or link to this item: http://repository.iitr.ac.in/handle/123456789/4109
Title: Synthesis and structural characterization of pincer type bicyclic diacyloxy- and diazaselenuranes
Authors: Selvakumar K.
Singh H.B.
Goel N.
Singh U.P.
Butcher R.J.
Published in: Dalton Transactions
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. © 2011 The Royal Society of Chemistry.
Citation: Dalton Transactions (2011), 40(38): 9858-9867
URI: https://doi.org/10.1039/c1dt10862j
http://repository.iitr.ac.in/handle/123456789/4109
Issue Date: 2011
ISSN: 14779226
Author Scopus IDs: 24173504100
35612432200
7102536856
57203181883
7201947292
Author Affiliations: Selvakumar, K., Department of Chemistry, Indian Institute of Technology Bombay, Powai Mumbai 400076, India
Singh, H.B., Department of Chemistry, Indian Institute of Technology Bombay, Powai Mumbai 400076, India
Goel, N., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India
Singh, U.P., Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee 247667, India
Butcher, R.J., Department of Chemistry, Howard University, Washington, DC 20059, United States
Corresponding Author: Singh, H.B.; Department of Chemistry, Indian Institute of Technology Bombay, Powai Mumbai 400076, India; email: chhbsia@chem.iitb.ac.in
Appears in Collections:Journal Publications [CY]

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