Electrophilic acetylation and bromination reactions of benzo[b]naphtho[2,3-e][1,4]dioxin |
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Authors: | Adam Pirko Michelle Crook Peter Sampson |
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Institution: | Adam Piórko,Michelle Crook,Peter Sampson |
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Abstract: | The reactivity of benzob]naphtho2,3-e]1,4]dioxin in the electrophilic aromatic substitution reactions has been studied. Friedel-Crafts acetylation resulted in the formation of three out of the possible five monoacetylated products, with the acetyl group located in positions 8 (major), 7 and 6 (minor) of the heterocycle. In the bromination reaction a higher selectivity was observed with the 6-bromo derivative found as the only monobrominated product and the 6,11-dibromo derivative found as the only polybrominated product. A ratio of unreacted heterocycle:6-bromo:6,11-dibromo derivatives in the bromination reaction has been found to depend strongly on the reaction conditions and on the heterocycle:bromine ratio. |
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