Skip to main content
Log in

Novel bromolactonization using N-bromophthalimide

  • Communications
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

Reaction of olefinic acids with N-bromophthalimide in dry N,N-dimethylformamide at room temperature gives bromolactones in good yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Literature Cited

  1. a) House, H. O.,Mordern Synthetic Reactions, 2nd ed., W. A. Benjamin, Calif., p. 441 (1972) and references cited therein; b) Barnett, W. E. and Needham, L. L., Halolactones from 1,4-dihydrobenzoic acids.J. Org. Chem.,40, 283(1975).

    Google Scholar 

  2. a) Corey, E. J. and Hase, T., Studies on the total synthesis of rifamycin; Highly stereoselective synthesis of intermediates for construction of the C(15) to C(29) chain.Tetra. Lett.,1979, 335; b) Corey, E. J. Trybulski, E. J., Melon, Jr., L. S., Nicolaou, K. C., Secrist, J. A., Lett, R., Sheldrake, P. W., Falck, J. R., Brunelle, D. J., Haslunger, M. F., Kim, Sunggak, Yoo, Sung-eun, Total synthesis of erythromycins 3.J. Am. Chem. Soc.,100, 4618 (1978).

    Google Scholar 

  3. a) Terashima, S. and Jew, S., Asymmetric halolactonization reaction; A highly efficient synthesis of optically active α-hydroxy acids from α, β-unsaturated acids.Tetra. Lett.,1977, 1005; b) Jew, S., Terashima, S., and Koga, K., Asymmetric halolactonization reaction-1.Tetrahedron,35, 2337 (1979); Jew, S., Terashima, S. and Koga, K., Asymmetric halolactonization reaction-2.Tetrahedron,35, 2345 (1979).

  4. a) Barnett, W. E. and Sohn, W. H., β-Lactones as kinetic products in the iodolactonization reaction.Chem. Comm.,1972, 472; b) Barnett, W. E. and Sohn, W. H. Formation of β-lactones in the iodolactonization reaction.Tetra. Lett.,1972, 1777.

  5. a) Alder, K., Chambers, F. W., and Trimborm, W., über die Dien-Synthese des Diphenylfulvens.Annalen,566, 27 (1950); b) Alder, K. and Ruhman, R., über die Dien-Synthese mit aliphatischen Fulvenen.Annalen.,566, 1 (1950).

    CAS  Google Scholar 

  6. a) Arnold, R. T., Campos, M. de M., and Lindsay, K. L., Participation of a neighboring carboxyl group in addition reactions. 1.J. Am. Chem. Soc.,75, 1044 (1953); b) Campos, M. de M., A gem-effect in the addition of 2,4-dinitrobenzenesulfenyl chloride to γ, δ-unsaturated acids.J. Am. Chem. Soc.,76, 4480 (1954).

    Article  CAS  Google Scholar 

  7. Mcquillan, J. F., Ord, W. O., and Simpson, P. L., Terpene synthesis. part IV. the synthesis of oxocyclohexanecarboxylic acids.J. Chem. Soc.,1964, 5526.

  8. Nicolaou, K. C., Claremon, D. A., Barnett, W. E., and Seitz, S. P., N-phenylselenophthalimide (N-PSP) and N-phenylselenosuccinimide (N-PSS). two versatile carriers of the phenylseleno group. oxyselenation of olefins and a selenium-based macrolide synthesis.J. Am. Chem. Soc.,101, 3704 (1979).

    Article  CAS  Google Scholar 

  9. a) Klein, J., The iodolactonization of cyclohexenacetic acids.J. Am. Chem. Soc.,81, 3611 (1959); b) House, H. O., Carlson, R. G., and Babad, Iodolactonization of 3-(3-cyclohexenyl) propionic acid.J. Org. Chem.,28, 3359 (1963); c) Linstead, R. P. and Williams, L. T. D., The chemistry of the three-carbon system. part VIII. tautomeric systems terminated by a phenyl group.J. Chem. Soc.,1926, 2735; d) Linstead, R. P., Noble, E. G., and Boorman, E. G., Investigations of the olefinic acids. part VII. the preparation of {ie139-1}.J. Chem. Soc.,1933, 557.

    Article  CAS  Google Scholar 

  10. All new compounds have been charcterized by IR and1H NMR spectroscopy.

  11. Cambie, R. C., Hayward, R. C., Roberts, J. L., and Rutledge, P. S., Iodolactonizations using thallium(1) carboxylates.J. Chem. Soc., Perkin I,1974, 1864.

    Google Scholar 

  12. Nicolaou, K. C., Sipio, S. P., and Blount, J. F., Phenylseleno-and phenylsulfenolactonizations. two highly efficient and synthetically useful cyclization procedures.J. Am. Chem. Soc.,101, 3884 (1979).

    Article  CAS  Google Scholar 

  13. Nicolaou, K. C., and Lysenko, Z., Phenylsulphenyl-lactonization.Chem. Comm.,1977, 293.

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Cook, Ch., Kang, Ek. Novel bromolactonization using N-bromophthalimide. Arch. Pharm. Res. 4, 137–139 (1981). https://doi.org/10.1007/BF02855758

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02855758

Keywords

Navigation