Synthesis,structures and reactivities of bis(triarylmethylium) dications and related diboranes

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Title: Synthesis,structures and reactivities of bis(triarylmethylium) dications and related diboranes
Author: Wang, Huadong
Abstract: The primary goal of the research described in this thesis concern the synthesis , characterization and study of 1 ,8 -bis (diarylmethylium )naphthalenediyl dications . Such dications have been prepared from the corresponding diols and have been fully characterized . Single crystals X -ray diffraction studies indicate that the two cationic centers of these derivatives are separated by 3 .0 - 3 .1 ? ? . The enforced proximity of the cationic centers intensifies the electron deficiency of these derivatives which behave as strong organic oxidants . As indicated by cyclic voltammetry , these dications undergo a two -electron reduction to afford the corresponding acenaphthenes . The newly formed C -C bond which links the former methylium are remarkably long (1 .628 -1 .706 ? ? . ) and can , in some instances , be oxidatively cleaved in the presence of acids . These dications can also be reduced chemically by reducing reagent , such as hydride , chloride , bromide and iodide . Remarkably , the reaction of 1 ,8 -bis (diphenylmethylium )naphthalenediyl dication with fluoride anion results in the formation of a mono fluorinated cation which features an unsymmetrical C -F ?C bridge between the former methylium centers . As indicated by 1H NMR spectroscopy , the structure of this cation is fluxional with the fluorine atom oscillating between the former methylium centers . Finally , this thesis also deals with the synthesis and study of 4 ,6 -bis (dimesitylboryl )dibenzofuran and isoelectronic dications .
URI: http : / /hdl .handle .net /1969 .1 /2716
Date: 2005-11-01

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Synthesis,structures and reactivities of bis(triarylmethylium) dications and related diboranes. Available electronically from http : / /hdl .handle .net /1969 .1 /2716 .

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