Synthesis of 5-substituted isoxazolidines by [3+2] cycloaddition of nitrones generated in an unusual way from nitrosobenzene and styrene /
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| Format: | Thesis eBook |
| Language: | English |
| Published: |
[College Station, Tex.] :
[Texas A&M University],
[2010]
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| Subjects: | |
| Online Access: | Link to OAK Trust copy |
| Abstract: | A 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+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. |
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| Item Description: | "Major Subject: Chemistry" Title from author supplied metadata (automated record created 2010-03-12 12:08:51). Electronic resource. |
| Physical Description: | 1 online resource. |
| Bibliography: | Includes bibliographical references. |