AI Article Synopsis
- Treatment of 5-nitroisocoumarin with aromatic acyl chlorides leads to the formation of 3-aryl-5-nitroisocoumarins instead of the anticipated 4-acyl-5-nitroisocoumarins.
- The reaction conditions were optimized, including a temperature of 150 degrees C, nitrobenzene as the solvent, and SnCl4 as the Lewis acid.
- The successful incorporation of [13C]-carbonyl from benzoyl chloride into the product confirmed that the carbon framework remained intact, specifically replacing the 3-C in the isocoumarin structure.
Article Abstract
Treatment of 5-nitroisocoumarin with aromatic acyl chlorides under Friedel-Crafts conditions gives 3-aryl-5-nitroisocoumarins, rather than the expected 4-acyl-5-nitroisocoumarins. This procedure was optimized for reaction temperature (150 degrees C), solvent (nitrobenzene), and Lewis acid (SnCl4). Reaction of 5-nitroisocoumarin with [13C]-carbonyl benzoyl chloride under the optimum conditions gave 5-nitro-3-phenylisocoumarin in which the 13C is located at the 3-C of the heterocycle, indicating that the benzoyl carbon framework is incorporated intact.
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| http://dx.doi.org/10.1021/jo0711236 | DOI Listing |
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