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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Bibliographic Details
Published inSynthetic communications Vol. 33; no. 17; pp. 3041 - 3048
Main Authors Salehi, Peyman, Khodaei, Mohammad Mahdi, Zolfigol, Mohammad Ali, Keyvan, Afsaneh
Format Journal Article
LanguageEnglish
Published NEW YORK Taylor & Francis Group 01.09.2003
Marcel Dekker Inc
Subjects
Chemistry
Chemistry, Organic
Epoxides
Magnesium hydrogensulfate
Physical Sciences
Science & Technology
Thiiranes
Vicinal diols
β-alkoxy alcohols
AMMONIUM THIOCYANATE
magnesium hydrogensulfate
STEREOSELECTIVE ALCOHOLYSIS
THIOUREA
HYDROLYSIS
vicinal diols
HIGHLY EFFICIENT
MILD
thiiranes
AMINES
beta-alkoxy alcohols
OXIRANES
epoxides
HETEROGENEOUS CONDITIONS
CHLORIDE
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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.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-120022479