• Archives of Pharmacal Research
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• v.5 no.2
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• pp.93-96
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• 1982

By using recemic 3-bromo-5-isobutyl-5-methylhydantoin (3a') in dry N, N-dimethylformamide which is a model reagent for asymmetric bromolactonization, bromolactonization of a series of olefinic acids was carried out to furnish corresponding bromolactones in moderate yields.

• Journal of the Korean Chemical Society
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• v.9 no.2
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• pp.88-95
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• 1965

The exo adduct between furfuryl derivatives (furan, furfuryl acetate and furfuryl alcohol) and maleic anhydride were prepared in the presence of ethyl ether. The bromination of the exo adduct of each derivatives gave a monobromolactone and dibromoacid when the reaction was done in the presence of water. The formation of the bromolactone was proved to be dependent to the carboxylic participation to the incipient rearranged carbonium ion of a classical type, and the participation was sterically hindered by the steric structure of the substituents. The bromination of the furan-maleic anhydride adduct in the presence of organic solvent $(CCl_4,\;CH_2Cl_2)$ gave the dibromide, whereas the photochlorination of the same adduct in the presence of carbon tetrachloride gave the tetrachloride. The procedure of the preparation and the reaction path of the halogenation were described.