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 CA 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.
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