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 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.
| Identifer | oai:union.ndltd.org:tamu.edu/oai:repository.tamu.edu:1969.1/ETD-TAMU-2008-12-82 |
| Date | 20 January 2010 |
| Creators | Kang, Jun Yong |
| Contributors | Connell, Brian T. |
| Source Sets | Texas A and M University |
| Language | en_US |
| Detected Language | English |
| Type | Book, Thesis, Electronic Thesis |
| Format | application/pdf |
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