Synthesis and Characterization of α,β-Unsaturated Hydroximoyl Chlorides and Hydroximates

James E. Johnson; Ling Lu; Houquan Dai; Diana C. Canseco; Krista M. Small; Debra D. Dolliver; Frank R. Fronczek

doi:10.1071/CH06188

RESEARCH ARTICLE

Synthesis and Characterization of α,β-Unsaturated Hydroximoyl Chlorides and Hydroximates

James E. Johnson ^A ^D , Ling Lu ^A , Houquan Dai ^A , Diana C. Canseco ^A , Krista M. Small ^A , Debra D. Dolliver ^B and Frank R. Fronczek ^C

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry and Physics, Texas Woman’s University, Denton, TX 76204, USA.

^B Department of Chemistry and Physics, Southeastern Louisiana University, Hammond, LA 70402, USA.

^C Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.

^D Corresponding author. Email: jjohnson@mail.twu.edu

Australian Journal of Chemistry 59(7) 439-444 https://doi.org/10.1071/CH06188
Submitted: 1 June 2006 Accepted: 20 July 2006 Published: 22 August 2006

Abstract

New α,β-unsaturated hydroximoyl chlorides (PhC(Cl)=CHC(Cl)=NOCH₃) and hydroximates (PhC(OCH₃)=CHC(OCH₃)=NOCH₃) were prepared. The ZZ-isomer of PhC(Cl)=CHC(Cl)=NOCH₃ was prepared in four steps from ethyl benzoylacetate. Ultraviolet irradiation of the ZZ-isomer gives a mixture of all four possible isomers. Sodium methoxide was reacted with these isomers to determine the configuration about the carbon–carbon double bond for each. The Z-isomers reacted with sodium methoxide to give the corresponding alkyne by elimination whereas the E-isomers gave the substitution product. The configuration about the carbon–nitrogen double bond was determined from the ¹H NMR chemical shift of the NOCH₃ group.

Acknowledgements

The Robert A. Welch Foundation (Grant Number M-020), the Minority Biomedical Research Support Program of the National Institutes of Health (NIH-MBRS Grant GM0825), and the Texas Woman’s University Research Enhancement Program supported this work. The South-Eastern Louisiana Faculty Development Grant Program is also acknowledged. The purchase of the diffractometer was made possible by grant no. LEQSF (1999–2000)-ENH-TR-13, administrated by the Louisiana Board of Regents.

References

Synthesis and Characterization of α,β-Unsaturated Hydroximoyl Chlorides and Hydroximates

Abstract

Acknowledgements

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