Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene
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 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.
Citation
Kang, Jun Yong (2008). Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene. Master's thesis, Texas A&M University. Available electronically from https : / /hdl .handle .net /1969 .1 /ETD -TAMU -2008 -12 -82.