Azetidin-2-one versus chroman-2-one: Application of (1)H-(13)C COSYNMR and mass spectroscopy in structure elucidation-class of compounds

Journal article

Authors / Editors

Pheko, Tshepo

Research Areas

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Publication Details

Author list: Singh GS, Pheko T

Publisher: Taylor & Francis: STM, Behavioural Science and Public Health Titles

Place: PHILADELPHIA

Publication year: 2008

Journal: Spectroscopy Letters (0038-7010)

Journal acronym: SPECTROSC LETT

Volume number: 41

Issue number: 1

Start page: 15

End page: 18

Number of pages: 4

ISSN: 0038-7010

eISSN: 1532-2289

Languages: English-Great Britain (EN-GB)

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Abstract

Azetidin-2-ones, commonly known as -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, (1)H NMR, and (13)C NMR spectra do not lead to unambiguous structure elucidation. This article reports a novel application of (1)H-(13)C 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.

Keywords

(1)H-(13)C COSYNMR, azetidin-2-one, chroman-2-one, mass spectroscopy

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