Aromatic ring strain in arylselenenyl bromides: role in facile synthesis of selenenate esters via intramolecular cyclization

Chemistry : a European Journal
K SelvakumarRay J Butcher

Abstract

The synthesis and reactivity of 2,6-disubstituted arylselenium compounds derived from 2-bromo-5-tert-butylisophthalic acid (43) are described. The syntheses of bis(5-tert-butylisophthalic acid dimethyl ester)diselenide (46) and bis(5-tert-butylisophthalic acid diisopropyl ester)diselenide (47) have been achieved by the reaction of the corresponding ester precursors with disodium diselenide. Reduction of diselenide 46 with lithium aluminum hydride affords 2,2'-bis(5-tert-butylbenzene-1,3-dimethanol)diselenide (53). Diselenides 46 and 47 exhibit intramolecular Se...O interaction. Compound 53 does not show any intramolecular Se...O interaction. The anomalous Se...O nonbonded coordination observed in the single-crystal X-ray structures of compounds 46, 47 and 53 is compared and contrasted. The corresponding selenenyl bromides 54 and 55, derived from the reaction of diselenides 46 and 47 with bromine, are quite stable in the solid state. However, they undergo hydrolysis and subsequent intramolecular cyclization upon heating or after having been kept in solution over a period of time to give the corresponding selenenate esters 56 and 57. The X-ray crystallographic study and density functional theory calculations on 54 at the B3LYP/6-...Continue Reading

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Citations

Sep 7, 2016·Journal of Theoretical Biology·Ramesh KheirabadiMohammad Reza Housiandokht
Nov 24, 2017·Metallomics : Integrated Biometal Science·Nilda V BarbosaJoão B T Rocha
Jun 27, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Varsha RaniRay J Butcher
Jan 3, 2019·Acta Crystallographica. Section C, Structural Chemistry·Krishnan VenkateshwaranRay J Butcher
Dec 5, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Alexandra PopCristian Silvestru
Mar 21, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Alpar PöllnitzAnca Silvestru
Jul 12, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Anca BeleagaCristian Silvestru
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May 31, 2011·Chemical Communications : Chem Comm·Vijay P SinghRay J Butcher
Mar 29, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Prakul RakeshJames A Golen
Aug 19, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·K SelvakumarRay J Butcher
Jun 1, 2013·Acta Crystallographica. Section E, Structure Reports Online·Gunay Z MammadovaVictor N Khrustalev

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