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Cyclopentadienones as intermediates for organic synthesis

Posted on:2004-12-24Degree:Ph.DType:Thesis
University:Case Western Reserve UniversityCandidate:Kim, Jin BumFull Text:PDF
GTID:2461390011976102Subject:Chemistry
Abstract/Summary:
An efficient method is described for cross coupling of alkynes by using a temporary silicon-tethered Fe(CO)5-promoted cyclocarbonylation. Silicon-tethered Fe(CO)5-promoted cyclocarbonylation consists of linking two alkynes into a silyl acetal, subjecting the resulting diyne to cyclocarbonylation and disengaging the metal and the tether moiety.; Chemistry of cyclopentadienones is studied in an effort to realize their potential utility in complex molecule synthesis.; Reactions of cyclopentadienones with Grignard reagents are described. The regioselectivities in the additions, where 1,2 and/or 1,4 adducts are obtained, are observed and speculations on the reasons for regioselectivity are presented.; Diels Alder reactions of cyclopentadienones with alkynes and arylalkynes are described. In principle, it is shown that substituted benzenes and biaryl structures can be synthesized from Diels-Alder reactions.
Keywords/Search Tags:Cyclopentadienones, Described, Alkynes
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