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Phosphorus Bearing Substrates In Ring Expansion Reactions, Bradley K. Norwood

Theses and Dissertations

A variety of substituted phosphonium salts, phosphorus ylides and phosphonates were studied to assess their utility in ring expansion reactions. The strategy involved formation of fused ring systems whose ring strain could be exploited to accomplish ring expansion to medium sized rings. β-Alkoxy vinylphosphonium salts were found to be unreactive with species such as the dimethylsulfoxonium methylide anion, Simmons-Smith type reagents. and carbenes in attempts to produce cyclopropyl phosphonium salts.

C-Alkylation of β-keto phosphorus ylides using haloalkanes bearing terminal groups that could be converted and reacted with the B-carbonyl, was also examined as a method for accessing strained rings bearing …