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Volumn 36, Issue 5, 2007, Pages 604-605

Unexpected ring-opening reaction of aziridine with acetic anhydride in DMF

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EID: 34250158071 PISSN: 03667022 EISSN: None Source Type: Journal
DOI: 10.1246/cl.2007.604 Document Type: Article

Times cited : (8)

References (25)

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- General procedure for the reaction of aziridine with acetic anhydride in DMF: acetic anhydride (1.0 equiv, was added to a solution of aziridine 1 (0.25 mmol) in DMF (2.0 mL, The reaction mixture was stirred at 80 or 110°C for a period of time indicated in Table 1. After the reaction was completed monitored by TLC, the mixture was cooled and washed with water and extracted with ethyl acetate. The organic extracts were dried (MgSO 4, filtered, and concentrated under reduced pressure. Purification by chromatography column on silica gel afforded the corresponding product. Data of selected example: trans-2-(4-methylphenylsulfonamido)cyclohexyl formate (3a, 1HNMR (CDCl3, 400 MHz) δ 1.15-1.45 (m, 4H, 1.60-1.75 (m, 2H, 1.90-2.05 (m, 2H, 2.42 (s, 3H, 3.20-3.30 (m, 1H, 4.65-4.75 (m, 1H, 5.22 (d, J, 8.3 Hz, 1H, 7.29 (d, J, 8.3 Hz, 2H, 7.58 (s, 1H, 7.75 (d, J, 8.3 Hz, 2H, 13C NMR CDCl
- 4S, 297.1035. Found, 297.1031.

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