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Synlett 2005(3): 489-490  
DOI: 10.1055/s-2005-862366
LETTER
© Georg Thieme Verlag Stuttgart · New York

Regioselective Ring-Opening of Aziridines with Thiophenol in the Presence of β-Cyclodextrin in Water [1]

M. Somi Reddy, M. Narender, K. Rama Rao*
Organic Chemistry Division I, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27160757; e-Mail: drkrrao@yahoo.com;
Further Information

Publication History

Received 16 December 2004
Publication Date:
04 February 2005 (online)

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Abstract

In the presence of β-cyclodextrin a variety of N-tosyl aziridines undergo ring-opening by thiophenols to afford the corresponding β-amino thiophenols in high yields with good regioselectivity.

Key words

aziridines - β-cyclodextrin - water - thiophenols - biomimetic - β-aminothiophenols

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IICT Communication no. 041207.

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IICT Communication no. 041207.

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General Procedure: β-CD (1 mmol) was dissolved in H2O (15 mL) and heated to 60 °C until a clear solution was formed. Then aziridine (1 mmol), dissolved in acetone (1 mL), was added drop-wise and the mixture allowed to react 50 °C. Thiophenol (1 mmol) was then added and the reaction mixture was stirred for 12 h at this temperature. The reaction mixture was extracted with EtOAc, dried, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (mesh 60-120) with EtOAc-hexane (1.2:8.8) as eluent.