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Title:I. Hexaiodobenzene Dication: A Ten-Electron Sigma-Delocalized Huckel-Aromatic Species. Ii. Synthesis and Study of Ortho-Bridged Triarylmethyl Compounds (Lithiation)
Author(s):Sagl, Dennis Joseph
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The synthesis of the bis trifluoromethanesulfonate salt of hexaiodobenzene dication is described. Experimental evidence supports the postulate that it is a ten-electron sigma-delocalized Huckel-aromatic species.
Syntheses of mono- and tri-tert-butyl substituted triphenylmethyl compounds with carbonyl groups bridging the ortho positions are described. Studies of the anions and radicals are described which indicate that the planarity enforced on these triphenylmethyl systems by the ortho-bridges and the (pi)-acceptor character of the carbonyl bridges give them unusual stability; furthermore, the tert-butyl groups provide increased solubility over the unsubstituted analogues. The isolation and properties of the first ionic hexaarylethane are also described.
The regiospecific lithiation of benzene rings ortho to various directing groups is a powerful synthetic method. The polylithiation of di- and triphenylmethanols and the reaction of the lithiated species with various electrophiles is described. The possible structures of the polylithiated intermediates is discussed in light of current theory regarding polylithio carbanions.
Issue Date:1986
Type:Text
Description:111 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1986.
URI:http://hdl.handle.net/2142/70354
Other Identifier(s):(UMI)AAI8701604
Date Available in IDEALS:2014-12-15
Date Deposited:1986


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