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