Abstract
A series of β-phenyl-2-isoxazolidineethanols having cis-disposed substituents at C(4) and C(5) has been prepared by asymmetric nitrone cycloaddition reactions and their NMR spectra recorded over a wide range of temperatures. The spectra in CDCl 3 at low temperatures indicate the presence of two interconverting invertomers for some of the tri-substituted isoxazolidines. The effect of H-bonding – intramolecular in CDCl 3 and intermolecular in CD 3OD – on the population ratio of the nitrogen invertomers has been investigated. The nitrogen inversion barriers are determined using complete line-shape analysis, and their dependence on solvent is discussed.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
