Unexpected Sultine Formation Resulting from the Friedel-Crafts Sulfonylation of Fluorene with 2,4,6-Triisopropylbenzenesulfonyl Chloride

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• Manuscript in preparation.
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• Analyses for 3: PDMS (DMSO/DCM): M+ - 432 amu; IR (KBr): v 1293 and 1144 cm−1; PTNMR (CDCl3): δ 1.14 (d, 12H, J-6.7 Hz), 1.26 (d, 6H, J-6.9 Hz), 2.91 (septet, 1H, J-6.9 Hz), 3.94 (s, 2H), 4.25 (septet, 2H, J-6.7 Hz), 7.17 (s, 2H), 7.39 (m, 2H), 7.58 (d, 1H), 7.75 (d, 1H), 7.82 (m, 2H), and 7.96 ppm (s, 1H); anal, calcd. for C28H32O2S (432.627): 77.7% C, 7.5% H, and 7.4% S; found: 76.3% C, 7.4% H, and 7.2% S. A sample recrystallized from 5% ethyl acetate/heptane melted at 164.6–165.5°C.
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• Analyses for 5: mp 75.0–76.5°C; FDMS (DMSO/DCM): M+ - 266 amu; FTIR (KBr): v 1140 and 1115 cm−1; FTNMR (CDC13): δ 1.28 (d, 6H, J-6.8 Hz), 1.37 (d, 6H, J-6.8 Hz), 1.65 (s, 3H), 1.85 (s, 3H), 2.99 (septet, 1H, J-6.8 Hz), 3.42 (septet, 1H, J-6.8 Hz), 6.93 (s, 1H), and 7.20 ppm (s, 1H); anal, calcd. for C15H22O2S (266.402): 67.6% C, 8.3% H, and 12.0% S; found: 67.8% C, 8.4% H, and 11.8% S.
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• Chemical Abstracts nomenclature: 4: 4,6-diisopropyl-2,2-dimethylbenzo [c]thiete 1,1-dioxide; 5: 5,7-diisopropyl-3,3-dlmethyl-benz[d]-2,1-oxathiole 1-orlde.
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• See ref. 7, and references cited therein
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