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Document Type : Short communication

Authors

1 Indian Institute of Integrative Medicine, Canal Road, Jammu Tawi 180001, India

2 Department of Chemistry, Govt. Degree College (Boys) Baramulla, Jammu and Kashmir, India

3 Department of Chemistry, Govt. Degree College (Boys) Sopore, Jammu and Kashmir, India

10.33945/SAMI/CHEMM.2019.5.9

Abstract

The reactions of glycals with N-iodosuccinimide and acetic anhydride under solvent free conditions provide 2-deoxy-2-iodo-α-mannopyranosyl acetates with good stereoselectivity. The developed process is in accordance with principles of green chemistry and addresses the shortage of such methods for the regioselective iodo acetoxylation of alkenes.

Graphical Abstract

Solvent Free Stereoselective Iodoacetoxylation of Alkenes and Glycals Using N-Iodosuccinimide and Acetic Anhydride

Keywords

Main Subjects

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[16] General procedure (for model reaction): In a round bottom flask containing appropriate amount of styrene (0.12 mL) and acetic anhydride (3 mL) and the contents stirred for 5 min. followed by the addition of NIS (292.5 mg) at 0 °C. The reaction mixture is allowed to stir at 0 °C for 30 minutes under solvent free conditions. On completion of the reaction, the contents were diluted with water, the organic layer separated and the aqueous portion extracted with DCM (3×50 mL).  The combined organic layer was washed with water (2×10 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure at
[17] Spectral data for Iodoacetate 4l: 1H NMR (500 MHz, CDCl3), d 6.43 (s, 1 H), 5.36 (broad s, 1 H), 4.83 (apparent t, J = 4.2 Hz, 1 H), 4.34 (m, 1 H), 4.23 (dd, J = 4.2, 0.7 Hz, 1 H), 4.18 (d, J = 6.8 Hz, 2 H), 2.12 (s, 3 H), 2.08 (s, 3 H), 2.02 (s, 3 H), 1.98 (s, 3 H); 13C NMR (100 MHz, CDCl3), 171.69, 170.8, 169.3, 168.0, 93.8, 69.81, 66.67, 62.3, 20.8, 20.7, 20.5, 18.8; IR (thin film), 1749, 1434, 1372, 1218, 1133, 1073, 1051, 994, 939 cm-1.