Carbon-14 kinetic isotope effects in the debromination of p-nitrodibromocinnamic acid

• Autorzy: Bukowski J. , Kanski R. , Kanska M.
• Języki publikacji: EN

Abstrakty

EN

The kinetic isotope effect (KIE) method was applied to study the mechanism of elimination of bromine from p-nitro-erythro-alfa,beta-dibromocinnamic acid labeled at the alfa-carbon. This compound was obtained starting from [2-14C]malonic acid via [2-14C]cinnamic acid and subsequent addition of bromide. The value of 14C KIE determined for alfa-position of side chain of p-nitro-erythro-alfa,beta-dibromocinamic acid proves that elimination of bromine leading to formation of (E)-p-nitrocinnamic acid proceeds via E2 mechanism.

Słowa kluczowe

EN

bromine; carbon-14; elimination; kinetic isotope effect; mechanism; p-nitrodibromocinnamic acid

• Wydawca: Institute of Nuclear Chemistry and Technology
• Czasopismo: Nukleonika
• Rocznik: 2002
• Tom: Vol. 47, nr 4
• Strony: 133--136
• Opis fizyczny: Bibliogr. 18 poz., rys.

Twórcy

autor

Bukowski J.

• Department of Chemistry, University of Warsaw, 1 Pasteura Str., 02-093 Warsaw, Poland, Tel.: [phone] ext. 321, Fax: [phone]

autor

Kanski R.

• Department of Chemistry, University of Warsaw, 1 Pasteura Str., 02-093 Warsaw, Poland, Tel.: [phone] ext. 321, Fax: [phone]

autor

Kanska M.

• Department of Chemistry, University of Warsaw, 1 Pasteura Str., 02-093 Warsaw, Poland, Tel.: [phone] ext. 321, Fax: [phone]

Bibliografia

• 1. Bennett GJ, Lee H-H, Das NP (1990) Biosynthesis of mangostin. Part 1: The origin of the xanthone skeleton. J Chem Soc Perkin Trans 1:2675−2685
• 2. Berman JD, Price CC (1958) Reaction of bromine with silver salts of some unsaturated acids. J Org Chem 23:102−103
• 3. Bukowski J, Kanski R, Kanska M (2002) Carbon-14 isotope effects in the debromination of dibromocinnamic acid. J Radioanal Nucl Chem 251:101−104
• 4. Bukowski J, Szul J, Kanski R, Kanska M (2000) Enzymatic synthesis of [3-14C]cinnamic acid. J Radioanal Nucl Chem 243:635−638
• 5. Eubanks JRI, Sims LB, Fry A (1991) Carbon isotope effect studies of the mechanism of the Hoffman elimination reaction of para-substituted (2-phenyl-1-14C)- and (2-phenyl-2-14C)trimethylammonium bromides. J Am Chem Soc 113:8821−8829
• 6. Fry A (1964) Application of the successive labelling technique to some carbon, nitrogen and chlorine isotope effect studies of organic reaction mechanisms. Pure Appl Chem 8:409−419
• 7. Fry A (1970) Heavy atom isotope effects in organic reaction mechanism studies. In: Collins CJ, Bowman NS (eds) Isotope effects in chemical reactions. Van Nostrand-Reinhold, New York, pp 364−414
• 8. Fry A, Sims LB, Eubanks JRI et al. (1983) Carbon-14 isotope effect studies of mechanisms of some elimination ractions. In: Duncan WP, Susän AB (eds) Synthesis and applications of isotopically labeled compounds. Elsevier, Amsterdam, pp 133−138
• 9. Grovenstein E Jr, Lee DE (1953) The stereochemistry and mechanism of the transformation of cinnamic acid dibromide to β-styrene. J Am Chem Soc 75:2639−2644
• 10. Hasan T, Sims LB, Fry A (1991) Heavy atom isotope effect studies of elimination reaction mechanism. 1. A kinetic and carbon-14 kinetic isotope effect studies of the base-promoted dehydrochlorination of substituted 1-phenylethyl-2-14C chlorides. J Am Chem Soc 105:3967−3975
• 11. Jemielity J, Kanska M, Kanski R (1998) Enzymatic synthesis of [1-13C]-, and [1-14C]-L-phenylalanine. Isotopes Environ Health Stud 34:335−339
• 12. Kwok WK, Mathai IM, Miller SI (1970) Debromination of meso- and DL-stilbene dibromide by lithium bromide in dimethylformamide. J Org Chem 35:3420−3423
• 13. Mathai IM, Miller SI (1970) Debromination of meso- and DL-stilbene dibromide by sodium iodide in dimethylformamide. J Org Chem 35:3416−3419
• 14. Murray A III, Williams DL (1958) Organic syntheses with isotopes. Vol. 1. Interscience Publ, New York
• 15. Tong JY, Yankwich PE (1957) Calculation of experimental isotope effects for pseudo first-order irreversible reactions. J Phys Chem 61:540−543
• 16. Trumbull ER, Finn RT, Ibne-Rasa KM, Sauers CK (1962) Kinetics of the decarboxylative elimination of cinnamic acid dibromides. J Org Chem 27:2339−2344
• 17. Trumbull ER, Ibne-Rasa KM (1963) Reaction of cinnamic acid dibromide with iodide ion. J Org Chem 28:1907−1909
• 18. Tüzün C, Malik KH (1974) Debromination of cinnamic acid dibromides by potassium iodide in 80% aqueous ethyl alcohol. Comm Sci Univ Ankara:1−12