Azetidin-2-one versus chroman-2-one

Application of 1H- 13C COSY NMR and mass spectroscopy in structure elucidation-class of compounds

Girija S. Singh, Tshepo Pheko

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Azetidin-2-ones, commonly known as β-lactams, constitute a biologically important class of compound. Treatment of azetidin-2-ones with alkali is known to form diverse types of compounds depending on the stability of the ring. In many cases, the ring is retained in the product at the cost of transformation of substituents. Spectroscopy is the most important tool to characterize the organic compounds. However, in some cases the structures of the products are so closely related that simple IR, 1H NMR, and 13C NMR spectra do not lead to unambiguous structure elucidation. This article reports a novel application of 1H-13C COSY NMR and mass spectroscopy in determining unequivocally an azetidin-2-one ring structure instead of a chroman-2-one ring structure for the product obtained by treatment of 1-benzhydryl-3,3-bis(4- methylphenyl)-4-[2-(o-dip-tolylacyl)hydroxyphenyl]-2-azetidinone with ethanolic sodium hydroxide at room temperature.

Original languageEnglish
Pages (from-to)15-18
Number of pages4
JournalSpectroscopy Letters
Volume41
Issue number1
DOIs
Publication statusPublished - Jan 1 2008

Fingerprint

Chromans
mass spectroscopy
ring structures
Nuclear magnetic resonance
Spectroscopy
nuclear magnetic resonance
products
spectroscopy
Lactams
Sodium Hydroxide
sodium hydroxides
rings
Alkalies
organic compounds
Organic compounds
alkalies
room temperature
Temperature

All Science Journal Classification (ASJC) codes

  • Spectroscopy

Cite this

@article{0dafbe18bd034c029eb2fa67f7453944,
title = "Azetidin-2-one versus chroman-2-one: Application of 1H- 13C COSY NMR and mass spectroscopy in structure elucidation-class of compounds",
abstract = "Azetidin-2-ones, commonly known as β-lactams, constitute a biologically important class of compound. Treatment of azetidin-2-ones with alkali is known to form diverse types of compounds depending on the stability of the ring. In many cases, the ring is retained in the product at the cost of transformation of substituents. Spectroscopy is the most important tool to characterize the organic compounds. However, in some cases the structures of the products are so closely related that simple IR, 1H NMR, and 13C NMR spectra do not lead to unambiguous structure elucidation. This article reports a novel application of 1H-13C COSY NMR and mass spectroscopy in determining unequivocally an azetidin-2-one ring structure instead of a chroman-2-one ring structure for the product obtained by treatment of 1-benzhydryl-3,3-bis(4- methylphenyl)-4-[2-(o-dip-tolylacyl)hydroxyphenyl]-2-azetidinone with ethanolic sodium hydroxide at room temperature.",
author = "Singh, {Girija S.} and Tshepo Pheko",
year = "2008",
month = "1",
day = "1",
doi = "10.1080/00387010701799613",
language = "English",
volume = "41",
pages = "15--18",
journal = "Spectroscopy Letters",
issn = "0038-7010",
publisher = "Taylor and Francis Ltd.",
number = "1",

}

Azetidin-2-one versus chroman-2-one : Application of 1H- 13C COSY NMR and mass spectroscopy in structure elucidation-class of compounds. / Singh, Girija S.; Pheko, Tshepo.

In: Spectroscopy Letters, Vol. 41, No. 1, 01.01.2008, p. 15-18.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Azetidin-2-one versus chroman-2-one

T2 - Application of 1H- 13C COSY NMR and mass spectroscopy in structure elucidation-class of compounds

AU - Singh, Girija S.

AU - Pheko, Tshepo

PY - 2008/1/1

Y1 - 2008/1/1

N2 - Azetidin-2-ones, commonly known as β-lactams, constitute a biologically important class of compound. Treatment of azetidin-2-ones with alkali is known to form diverse types of compounds depending on the stability of the ring. In many cases, the ring is retained in the product at the cost of transformation of substituents. Spectroscopy is the most important tool to characterize the organic compounds. However, in some cases the structures of the products are so closely related that simple IR, 1H NMR, and 13C NMR spectra do not lead to unambiguous structure elucidation. This article reports a novel application of 1H-13C COSY NMR and mass spectroscopy in determining unequivocally an azetidin-2-one ring structure instead of a chroman-2-one ring structure for the product obtained by treatment of 1-benzhydryl-3,3-bis(4- methylphenyl)-4-[2-(o-dip-tolylacyl)hydroxyphenyl]-2-azetidinone with ethanolic sodium hydroxide at room temperature.

AB - Azetidin-2-ones, commonly known as β-lactams, constitute a biologically important class of compound. Treatment of azetidin-2-ones with alkali is known to form diverse types of compounds depending on the stability of the ring. In many cases, the ring is retained in the product at the cost of transformation of substituents. Spectroscopy is the most important tool to characterize the organic compounds. However, in some cases the structures of the products are so closely related that simple IR, 1H NMR, and 13C NMR spectra do not lead to unambiguous structure elucidation. This article reports a novel application of 1H-13C COSY NMR and mass spectroscopy in determining unequivocally an azetidin-2-one ring structure instead of a chroman-2-one ring structure for the product obtained by treatment of 1-benzhydryl-3,3-bis(4- methylphenyl)-4-[2-(o-dip-tolylacyl)hydroxyphenyl]-2-azetidinone with ethanolic sodium hydroxide at room temperature.

UR - http://www.scopus.com/inward/record.url?scp=42249099027&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=42249099027&partnerID=8YFLogxK

U2 - 10.1080/00387010701799613

DO - 10.1080/00387010701799613

M3 - Article

VL - 41

SP - 15

EP - 18

JO - Spectroscopy Letters

JF - Spectroscopy Letters

SN - 0038-7010

IS - 1

ER -