19744-05-9Relevant academic research and scientific papers
5-Acetoxy-2,3-diphenylisoxazolidine and 5-acetoxy-3-(4-nitrophenyl)-2-phenylisoxazolidine
Mukherjee, Shubhasish,Parmar, Virinder S.,Errington, William
, p. 1829 - 1831 (1999)
The configurations of the isoxazolidine rings in the title compounds, 2,3-diphenylisoxazolidin-5-yl acetate (C17H17NO3), (I), and 3-(4-nitrophenyl)-2-phenylisoxazolidin-5-yl acetate (C17H16N2/su
Hydrophobic effect on 1,3-dipolar cycloaddition reactions
Pandey, Pramod S.,Pandey, Inder K.
, p. 7237 - 7240 (2007/10/03)
Rate and selectivity of 1,3-dipolar cyloaddition reactions of C,N-diphenylnitrone are influenced by hydrophobic effect.
An efficient C2-homologation of aromatic aldehydes via 5-hydroxyisoxazolidines
Di Nunno,Scilimati
, p. 4121 - 4132 (2007/10/02)
The reaction of lithium enolate of acetaldehyde (generated by the known cycloreversion of THF in the presence of n-BuLi) with a number of aryl N-phenylnitrones affords 2-phenyl-3-aryl-5-hydroxyisoxazolidines (trans + cis) in high yields. A low conversion or no reaction at all were instead observed with some N-alkylnitrones (methyl and t-butyl, respectively). Base (or acid) induced decomposition of 5-hydroxyisoxazolidines allows cinnamaldehydes to be obtained in high yields. Thus the combination of the synthesis and decomposition of 5-hydroxyisoxazolidines provides a new efficient way for the C2-homologation of aromatic aldehydes.
Determination of Configuration and Conformation of Isoxazolidines by Nuclear Overhauser Effect Difference Spectroscopy
DeShong, Philip,Dicken, C. Michael,Staib, Ronald R.,Freyer, Alan J.,Weinreb, Steven M.
, p. 4397 - 4403 (2007/10/02)
The configurations of isoxazolidines 2, 3, 5, 7, and 10-12 have been assigned by analysis of NMR coupling constants and by nuclear Overhauser effect difference spectroscopy (NOEDS).The preferred solution conformations of isoxazolidines 3 and 5 were determined to be as in 3A/5A.It is proposed that these conformations are adopted to take advantage of the anomeric effect and to alleviate the unfavorable stereoelectronic lone pair-lone pair interaction in the N-O portion of the molecule (gauche effect).
