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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Date
2009
Author
Mazimba, O.
Majinda, R.R.
Masesane, I.B.
Publisher
Elsevier Science Ltd, http://www.elsevier.com/locate/tetlet
Link
http://ac.els-cdn.com/S0040403909015895/1-s2.0-S0040403909015895-main.pdf?_tid=d36f06ff4a8a181084144252b430c73c&acdnat=1343892896_56b592aa5e05200086b4a429be850927
Type
Published Article
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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.
URI
http://hdl.handle.net/10311/1026
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