Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
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


[1]   The Merck Index 12th edn 1996 (Merck and Co.: Whitehouse Station, NJ).

[2]   C. M. Henry, Chem. Eng. News 2000, 78 (March 6),  41.
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
         
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  
        | Crossref |  GoogleScholarGoogle Scholar |  open url image1

[26]   T. H. Lowry, K. S. Richardson, Mechanism and Theory in Organic Chemistry 1987, p. 616 (Harper and Rowe: New York, NY).

[27]   F. A. Carroll, Perspectives on Structure and Mechanism in Organic Chemistry 1998, p. 661 (Brooks Cole: Pacific Grove, CA).