An unexpected 1,2-hydride shift in phosphoric acid-promoted cyclodimerization of styrene oxides under solvent-free conditions. A synthetic route towards 2,4-disubstituted 1,3-dioxolanes
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Author list: Mazimba O, Majinda RR, Masesane IB
Publisher: Elsevier
Place: OXFORD
Publication year: 2009
Journal: Tetrahedron Letters (0040-4039)
Journal acronym: TETRAHEDRON LETT
Volume number: 50
Issue number: 43
Start page: 5927
End page: 5929
Number of pages: 3
ISSN: 0040-4039
Languages: English-Great Britain (EN-GB)
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Abstract
A 1,2-hydride shift in the phosphoric acid-promoted cyclodimerization of styrene oxide and its chloro derivatives under solvent-free conditions leading to 2,4-disubstituted 1,3-dioxolanes is described. Methoxy substituents on the aromatic ring of the styrene oxide prevent the 1,2-hydride shift reaction leading to substituted 1,4-dioxanes. A possible mechanism for the formation of the 1,3-dioxolanes is proposed. (C) 2009 Elsevier Ltd. All rights reserved.
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