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Synthesis 2009(19): 3267-3278  
DOI: 10.1055/s-0029-1216960
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Pot Synthesis of β-Amino/β-Hydroxy Selenides and Sulfides from Aziridines and Epoxides

Venkataraman Ganesh, Srinivasan Chandrasekaran*
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, Karnataka, India
Fax: +91(80)23602423; e-Mail: scn@orgchem.iisc.ernet.in;
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Publication History

Received 14 April 2009
Publication Date:
21 August 2009 (online)

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Abstract

Diaryl disulfides and diselenides undergo facile cleavage on treatment with rongalite (sodium hydroxymethanesulfinate) to generate the corresponding thiolate and selenolate species in situ, which effect the ring opening of aziridines and epoxides in a regio­selective manner. A simple, mild, cost-effective protocol has been developed to prepare β-amino and β-hydroxy sulfides and selenides in a one-pot operation.

Key words

β-amino selenide - β-amino sulfide - β-hydroxy selen­ide - β-hydroxy sulfide - rongalite - aziridine - epoxide

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15

After the addition of rongalite, the mixture turned orange yellow in the case of diselenides, due to the formation of selenolate ion and yellow in the case of disulfides, due to formation of the thiolate. The color disappeared at the completion of the reaction.

19

The ratio of regioisomers was determined based on the integration values of ¹H NMR.