Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene

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dc.contributorConnell, Brian T.
dc.creatorKang, Jun Yong
dc.date.accessioned2010-01-20T21:15:08Z
dc.date.accessioned2017-04-07T19:57:00Z
dc.date.available2010-01-20T21:15:08Z
dc.date.available2017-04-07T19:57:00Z
dc.date.created2008-12
dc.date.issued2010-01-20
dc.description.abstractA new synthetic method toward 5-substituted isoxazolidines by [3 plus 2] cycloaddition of nitrones generated from nitrosobenzene and styrene was discovered. The formation of nitrones from nitrosobenzene and mono-substituted aromatic styrenes was demonstrated. The cycloaddition reactions between styrenes and nitrosobenzenes work well when a moderate excess of styrenes was employed. The labeling studies support that cleavage of the styrene double bond occurred and accounted for all the carbons in the starting materials and products. A [3 plus 2] dipolar cycloaddition is implicated by the available mechanistic data and allows for the rapid assembly of various substituted isoxazolidines directly from nitrosobenzenes, electron deficient alkenes, and styrene.
dc.identifier.urihttp://hdl.handle.net/1969.1/ETD-TAMU-2008-12-82
dc.language.isoen_US
dc.subject[3+2] dipolar cycloaddition
dc.subjectisoxazolidine
dc.subjectnitrone
dc.titleSynthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene
dc.typeBook
dc.typeThesis

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