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Applications of transition metal chemistry toward the synthesis of highly functionalized cyclopentenones, benzoquinones, and bisquaryls

Posted on:1995-09-13Degree:Ph.DType:Thesis
University:Emory UniversityCandidate:Yu, Richard Hung ChiuFull Text:PDF
GTID:2461390014488921Subject:Organic Chemistry
Abstract/Summary:
Highly stereoselective and regioselective addition was observed upon reaction of nucleophiles with cationic molybdenum ;The synthesis, full characterization, and physical characteristics of the novel compound 4,4;A new class of compounds, bis(stannyl)quinones, were synthesized through the use of cyclobutenedione chemistry. These 2,3-bis(trialkylstannyl)-5,6-disubstituted-1,4-benzoquinones underwent facile mono- or sequential Stille cross-coupling reactions which provided different functionalities on the quinone unit that were previously unavailable. Furthermore, the unsymmetrical, bis(stannyl)quinone, 2-(tricyclohexylstannyl)-3-(trimethylstannyl)6-methyl-5-(1-methylethoxy)-1,4-benzoquinone, was constructed. With sterically different tin moieties, the Stille cross-coupling reaction was selectively favored at the carbon bearing the trimethyltin moiety in a 30:1 ratio.
Keywords/Search Tags:Stille cross-coupling
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