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Reactivity of the double bond in coumarins and related unsaturated carbonyl compounds

Part VII. Action of mercuric acetate on hydroxy and 4-methyl coumarins

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Summary

The action of mercuric acetate in methyl alcoholic solution on (1) umbelliferone, (2) 4-methylumbelliferone and (3) 4: 7-dimethylcoumarin has been investigated. With umbelliferone addition at the double bond and substitution in positions 6 and 8 take place whereas in the case of its 4-methyl derivative position 8 alone is mercurated to yield a monoacetoxymercuri-compound. In regard to the last compound the reaction stops with addition at the double bond and mercuration of the 6th position, the position 8 escaping the attack of the reagent. It is concluded that owing to the influence of the substitutent groups the reactivity of the three active centres of the coumarin molecule are differently affected.

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References

  1. Seshadri and Suryaprakasa RaoProc. Ind. Acad. Sci., (A), 1936,4, 162.

    Google Scholar 

  2. PosenBer., 1881,14, 2747.

    Google Scholar 

  3. Seshadri and Suryaprakasa RaoProc. Ind. Acad. Sci., (A), 1936,3, 293.

    Google Scholar 

  4. Sen and ChakravartiJ.I.C.S., 1929, 847.

  5. Naik and PatelJ.C.S., 1934, 1043.

  6. Pechmann and ObermillerBer., 1901,34, 660.

    Google Scholar 

  7. Rangaswami and SeshadriProc. Ind. Acad. Sci., (A), 1937,6, 112.

    Google Scholar 

  8. ClaytonJ.C.S., 1908, 528.

  9. Simmonis, H.Die Cumarine, p. 155.

  10. ClaytonJ.C.S., 1910,97, 1391.

    Google Scholar 

  11. Murty, Rao and SeshadriProc. Ind. Acad. Sci., (A), 1937,6, 316.

    Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Andhra University, Waltair

    P. Suryaprakasa Rao, V. D. Nageswara Sastri & T. R. Seshadri

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  1. P. Suryaprakasa Rao
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  2. V. D. Nageswara Sastri
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  3. T. R. Seshadri
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Rao, P.S., Sastri, V.D.N. & Seshadri, T.R. Reactivity of the double bond in coumarins and related unsaturated carbonyl compounds. Proc. Indian Acad. Sci. (Math. Sci.) 9, 22–28 (1939). https://doi.org/10.1007/BF03045446

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  • DOI: https://doi.org/10.1007/BF03045446

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