l-Chloro-2-(JV-chIoro-p-toluenesulfonamido)acenaphthene. To a well-stirred cold (0-2 °C) solution of 2.01 g of acenaphthylene in 15 mL of CH2C12 was added dropwise (10 min) a solution of 3.2 g of Cl2NTs in 15 mL of CH2C12. Workup as described above followed except that CC14 at -30 °C was used in place of ether at 0-2 °C to triturate the crude solid. The insoluble portion (0.9 g, mp 149-152 °C) was identified as 1chloro-2-p-toluenesulfonamidoacenaphthene (see below). The CC14 filtrate was evaporated and the residue was triturated with 15 mL of ether. Cooling to -30 °C (dry ice-acetone bath) gave a light-yellow solid, which was washed with two 3-mL portions of cold (-20 °C) ether to give 2.1 g (59.2%) of the N-chloro compound, mp 115-117 °C. The analytical sample had the following: mp 117-119 °C (ether); IR (CHC13) 1340, 1160 cm-1 (S02);
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