Synthesis and NMR Spectroscopic Characterization of Some Fluoro-2H-1-Benzopyran Derivatives

Yannick Teral; Gabriel Roubaud; Claude Aubert; Robert Faure; Mylène Campredon

doi:10.1071/CH05062

RESEARCH ARTICLE

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Synthesis and NMR Spectroscopic Characterization of Some Fluoro-2H-1-Benzopyran Derivatives

Yannick Teral ^A , Gabriel Roubaud ^B , Claude Aubert ^C , Robert Faure ^B and Mylène Campredon ^A ^D

+ Author Affiliations

- Author Affiliations

^A JE 2421 TRACES, Université de la Méditerranée, Faculté des Sciences de Luminy, 13298 Marseille Cedex 9, France.

^B UMR-CNRS-6178, Faculté des Sciences de St Jérome, Université Paul Cézanne, 13397 Marseille Cedex 13, France.

^C UPRES EA 3286, Faculté de Pharmacie de la Timone, Université de la Méditerranée, 13385 Marseille Cedex 5, France.

^D Corresponding author. Email: Mylene.Campredon@luminy.univ-mrs.fr

Australian Journal of Chemistry 58(7) 517-521 https://doi.org/10.1071/CH05062
Submitted: 24 February 2005 Accepted: 13 May 2005 Published: 21 July 2005

Abstract

The synthesis of some new fluoro-2H-1-benzopyran derivatives utilizing a reaction between titanium phenolates and β-phenylcinnamaldehydes in toluene is reported. These compounds were characterized by NMR and UV/visible spectroscopy as well as mass spectrometry. In solution all the compounds are photochromic. Complete assignment of the ¹H and ¹³C resonances was achieved by concerted application of homonuclear (gs-COSY), proton-detected (C, H) one-bond (gs-HMQC), and long-range (gs-HMBC) heteronuclear two-dimensional chemical shift correlation experiments using a 500 MHz NMR spectrometer equipped with a cryoplatform and a 5 mm cryoprobe. The mass spectra of the different compounds were characterized by intense molecular and high fragment ions. The introduction of an atom of fluorine as a molecular probe is of interest in determining the mechanistic aspects of the photochemical process.

Acknowledgments

We thank Dr J. C. Arnall-Culliford for helpful discussions.

References

Synthesis and NMR Spectroscopic Characterization of Some Fluoro-2H-1-Benzopyran Derivatives

Abstract

Acknowledgments

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