Magnesium Hydrogensulfate: A Cheap and Efficient Catalyst for the Conversion of Epoxides into β-Alkoxy Alcohols, Vicinal-Diols, and Thiiranes
The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of magnesium hydrogensulfate, Mg(HSO 4 ) 2 , with high degree of regioselectivity. The reactions are chemoselective and many of the other functional group...
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Published in | Synthetic communications Vol. 33; no. 17; pp. 3041 - 3048 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
NEW YORK
Taylor & Francis Group
01.09.2003
Marcel Dekker Inc |
Subjects | |
Online Access | Get full text |
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Summary: | The nucleophilic ring opening reactions of epoxides by aliphatic alcohols and water are achieved efficiently in the presence of catalytic amounts of magnesium hydrogensulfate, Mg(HSO
4
)
2
, with high degree of regioselectivity. The reactions are chemoselective and many of the other functional groups such as ethereal carbon-oxygen bonds as well as carbon-carbon double bond remain intact under the reaction conditions. Epoxides also react with thiourea or ammonium thiocyanate in the presence of Mg(HSO
4
)
2
to afford the corresponding thiiranes in good to excellent yields. |
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ISSN: | 0039-7911 1532-2432 |
DOI: | 10.1081/SCC-120022479 |