Study of inversion isomerism in some 4,5-trans- substituted isoxazolidines by NMR spectroscopy

Shaikh A. Ali; M. I.M. Wazeer

Study of inversion isomerism in some 4,5-trans- substituted isoxazolidines by NMR spectroscopy

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

A series of β-phenyl-2-isoxazolidineethanols having trans-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 CDCl₃ at low temperatures indicate the presence of a single invertomer for most of the trisubstituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl₃ and intermolecular in CD₃OD - 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.

Original language	English
Pages (from-to)	15-28
Number of pages	14
Journal	Asian Journal of Spectroscopy
Volume	12
Issue number	1
State	Published - 2008

Keywords

Inversion barriers
Invertomers
Isoxazoldines
Nitrogen inversion

ASJC Scopus subject areas

Spectroscopy

Cite this

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title = "Study of inversion isomerism in some 4,5-trans- substituted isoxazolidines by NMR spectroscopy",

abstract = "A series of β-phenyl-2-isoxazolidineethanols having trans-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 CDCl3 at low temperatures indicate the presence of a single invertomer for most of the trisubstituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - 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.",

keywords = "Inversion barriers, Invertomers, Isoxazoldines, Nitrogen inversion",

author = "Ali, \{Shaikh A.\} and Wazeer, \{M. I.M.\}",

year = "2008",

language = "English",

volume = "12",

pages = "15--28",

journal = "Asian Journal of Spectroscopy",

issn = "0971-9237",

number = "1",

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TY - JOUR

T1 - Study of inversion isomerism in some 4,5-trans- substituted isoxazolidines by NMR spectroscopy

AU - Ali, Shaikh A.

AU - Wazeer, M. I.M.

PY - 2008

Y1 - 2008

N2 - A series of β-phenyl-2-isoxazolidineethanols having trans-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 CDCl3 at low temperatures indicate the presence of a single invertomer for most of the trisubstituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - 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.

AB - A series of β-phenyl-2-isoxazolidineethanols having trans-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 CDCl3 at low temperatures indicate the presence of a single invertomer for most of the trisubstituted isoxazolidines. The effect of H-bonding - intramolecular in CDCl3 and intermolecular in CD3OD - 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.

KW - Inversion barriers

KW - Invertomers

KW - Isoxazoldines

KW - Nitrogen inversion

UR - https://www.scopus.com/pages/publications/41949116891

M3 - Article

AN - SCOPUS:41949116891

SN - 0971-9237

VL - 12

SP - 15

EP - 28

JO - Asian Journal of Spectroscopy

JF - Asian Journal of Spectroscopy

IS - 1

ER -

Study of inversion isomerism in some 4,5-trans- substituted isoxazolidines by NMR spectroscopy

Abstract

Keywords

ASJC Scopus subject areas

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