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General Method for the Synthesis of 1-Arenesulfonylazetidines: The pertinent aziridine (1 mmol, trimethylsulfoxonium iodide (3 mmol) and KOH (3 mmol) were loaded on neutral alumina (0.5 mmol) solid support. This mixture was irradiated with microwaves for the specified time (Table 1, Only a single product (as shown by TLC) was formed. The reaction was quenched by addition of cold H2O. The product was extracted with EtOAc and purified by simple crystallization or through column chromatography on silica gel. cis-2-Methyl-3-phenyl-1-(4-toluenesulfonyl)azetidine (3f, white crystalline solid; mp 105-106°C; yield: 79, IR: 1333, 1164 (SO 2) cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.65 (m, 5 H, 7.32 (s, 4 H, 4.26 (q, J, 7 Hz, 1 H, 3.93 (distorted d, J, 6 Hz, 2 H, 3.41 (m, 1 H, 2.39 (s, 3 H, 0.98 (d, J, 7 Hz, 3 H, 13C NMR 75 MHz, CDCl3, δ, 127.2-137
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+].
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34
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38549169806
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The reaction vials were placed in the MW reactor supplied with a safety valve for release of overpressure
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The reaction vials were placed in the MW reactor supplied with a safety valve for release of overpressure.
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35
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38549161448
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After the set temperature of 90°C is reached, the power regulates itself to maintain the reaction temperature.
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After the set temperature of 90°C is reached, the power regulates itself to maintain the reaction temperature.
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