Abstract
A series of 9- exo-halo tetracyclic lactones was prepared through the reaction of chlorine, bromine and iodine in aqueous sodium bicarbonate with endo- cis-3-trichloroacetylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid lactol ( 1). Reaction of 1 with peracetic acid formed the corresponding hydroxy derivative. Addition of bromine to lactol 1 in carbon tetrachloride gives exclusively the exo- cis-dibromide addition product. Hydrolysis of chloro and bromo tetracyclic lactones 3 and 4 with 5% sodium hydroxide gives endo- cis-5,6-dihydroxybicyclo[2.2.1]heptane-2,3-dicarboxylic acid dilactone ( 11). Reaction of iodo derivative 5 with one or two equivalents of sodium hydroxide gives dilactone 11; but with 5% sodium hydroxide the product is endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid anhydride ( 16). Reaction of 5 with sodium iodide in acetone gives lactol 1, anhydride 16, and starting material. The mechanistic implications are discussed.
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