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Separation and Structural Assignment of the Cis and Trans Isomers of S-(2,3-dichloroallyl)diisopropylthiocarbamate (diallate)

Published online by Cambridge University Press:  12 June 2017

F. H. A. Rummens
F. H. A. Rummens*
Affiliation:
Dept. of Chemistry, Univ. of Regina, Regina Sask. S4S 0A2, Canada
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Abstract

The two isomers of diallate [S-2,3-dichloroallyl)diisopropylthiocarbamate] can be isolated by preparative scale gas chromatography using a Carbowax 20M liquid phase. on the basis of IR and NMR spectroscopic and other evidence the isomer with the shorter retention time is assigned the trans configuration and that with the longer retention time is assigned the cis configuration.

Type
Research Article
Information
Weed Science , Volume 23 , Issue 1 , January 1975 , pp. 7 - 10
Copyright
Copyright © 1975 by the Weed Science Society of America 

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References

Literature Cited

1. Barfield, M. and Chakrabarti, B. 1969. Long Range proton spin-spin coupling. Chem. Rev. 69:757–778.Google Scholar
2. Bernstein, H.J. and Powling, J. 1951. The cis and trans isomers of 1,2-dichloro-1-propene. J. Amer. Chem. Soc. 73:1843–1844.CrossRefGoogle Scholar
3. Boonstra, H.J. and Rinzema, L.C. 1960. Infrared absorption spectra of alkylthio compounds. Rec. Trav. Chim. Pays Bas 79:962–976.Google Scholar
4. Harman, M.W. and D'Amico, J.J. 1967. U.S. Patent (to Monsanto Chemical Co.) 3,330,643, July 11th; Chem. Abstr. 67:108271 m.Google Scholar
5. Hatch, L.F., D'Amico, J.J., Ruhnke, E.V. 1952. Allylic chlorides XV; Preparation and Properties of the 1,2,3-trichloropropenes. J. Amer. Chem. Soc. 74:123–126.Google Scholar
6. Kampmeyer, J.A. and Chen, G. 1965. The stereochemistry of the free-radical addition of thiol-acetic acid to 1-hexyne. J. Amer. Chem. Soc. 87:2608–2613.Google Scholar
7. King, W.H. and Smith, H.A. 1950. The dipole moments of the isomeric dichloropropenes. J. Amer. Chem. Soc. 72:3459–3462.Google Scholar
8. Martin, G.J. and Martin, M.L. 1972. The stereochemistry of double bonds. Progress in Nuclear Magnetic Resonance 8:63–259.Google Scholar
9. Onley, J.H. and Yip, G. 1971. Herbicidal carbamates: extraction, clean-up and gas-chromatographic determination by thermionic, electron capture and flame photometric detectors. J. Assoc. Offic. Anal. Chem. 54:1366–1370.Google Scholar
10. Pascual, C., Meier, J., Simon, W. 1966. Regel zur Abschätzung der chemischen Verschiebung von Protonen an einer Doppelbindung. Helv. Chim. Acta 49:164–168.Google Scholar
11. Rummens, F.H.A. 1965. Assignment of cis and trans configurations in tri-alkylated ethylenes by infrared spectroscopy. Rec. Trav. Chim. Pays Bas 84:1003–1008.Google Scholar
12. Tobey, S.W. 1969. Structure assignments in polysubstituted ethylenes by Nuclear Magnetic Resonance. J. Org. Chem. 34:1281–1298.Google Scholar
13. Truce, W.E. and Boudakian, M.M. 1956. The mechanism of the base-catalyzed reaction of vinylidenechloride with thiols. J. Amer. Chem. Soc. 78:2748–2751.Google Scholar
14. Vernetti, J. and Freed, V.H. 1964. Geometric isomers of S-2,3-dichloroallyl N,N-diisopropyl thiolcarbamate and their biological activity. Abstr. Weed Soc. Amer. p. 75.Google Scholar